CAS: 816444-90-3; (1R,2S,5S)-3-((S)-2-(3-Tert-Butylureido)-3,3-Dimethylbutanoyl)-6,6-Dimethyl-3-Azabicyclo[3.1.0]Hexane-2-Carboxylic Acid

该化合物是其复杂的双环结构,包括环内的一个氮原子,表明它是一个aza化合物.多种手性中心的存在有助于其立体化学,对于其生物活动和与生物目标的相互作用至关重要.三丁基和二甲基组表明该分子有相当大的消毒成分,有可能影响其溶性与再活性.此外,氨基酸功能组表明,它可以参与酸基反应,并可能在生物系统中的束缚性互动方面发挥作用.这种化合物可能有益于医药化学,特别是药物的研发,因为其独特的结构特征和潜在生物活动.其具体特性,如溶性,熔点等,其具体性需要.

英文名称(1R,2S,5S)-3-((S)-2-(3-Tert-Butylureido)-3,3-Dimethylbutanoyl)-6,6-Dimethyl-3-Azabicyclo[3.1.0]Hexane-2-Carboxylic Acid
中文名称(1R,2S,5S)-3-[(2S)-2-[[[(叔丁基)氨基]羰基]氨基]-3,3-二甲基-1-氧代丁基]-6,6-二甲基-3-氮杂双环[3.1.0]己烷-2-羧酸
CAS编号816444-90-3
MFCD编号:MFCD11865139
FDA UNII编号:QX2Y9CCT6J
分子式:C19H33N3O4分子量:367.48
产品CID: 1809340
产品分类有机原料 → 羧酸类化合物及衍生物

相似结构搜索
InChIKey: ODCGBMOBUUHGRG-ZDEQEGDKSA-N
1S/C19H33N3O4/c1-17(2,3)13(20-16(26)21-18(4,5)6)14(23)22-9-10-11(19(10,7)8)12(22)15(24)25/h10-13H,9H2,1-8H3,(H,24,25)(H2,20,21,26)/t10-,11-,12-,13+/m0/s1
计算化学: 氢键受体数4.0氢键供体数3.0可旋转键数5.0

MSDS等安全信息

上下游产品

CAS号394735-28-5 (1R,2S,5S)-N-(4... | CAS号394730-60-0 波普瑞韦 | CAS号3651-67-0 4-甲基吗啉盐酸盐

合成工艺路线路线简述

合成目标产物 (1R,2S,5S)-3-[(S)-2-(3-Tert-Butyl-Ureido)-3,3-Dimethyl-Butyryl]-6,6-Dimethyl-3-Aza-Bicyclo[3.1.0]Hexane-2-Carboxylic Acid 主要起始原料 N-[[(1,1-Dimethylethyl)Amino]Carbonyl]-3-Methyl-L-Valine
394735-27-4 = 816444-90-3
反应条件:1.1 Reagents: Potassium Hydroxide,Tetrabutylammonium Hydroxide Solvents: Toluene,Water; 0 - 10 °C; 10 °C -> 30 °C; 4 H,25 - 30 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 2
标题:Synthesis And Process Optimization Of Boceprevir: A Protease Inhibitor Drug
作者:Bhalerao,Dinesh S.; Et Al
参考文献:Organic Process Research & Development 日期:2015 卷标:19(11) 页码:1559-1567]

1373205-30-1 + 101968-85-8 = 816444-90-3
反应条件:1.1 Reagents: 4-Methylmorpholine,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Solvents: Dimethylformamide,Toluene; 0 - 10 °C
标题:Synthesis And Process Optimization Of Boceprevir: A Protease Inhibitor Drug
作者:Bhalerao,Dinesh S.; Et Al
参考文献:Organic Process Research & Development 日期:2015 卷标:19(11) 页码:1559-1567]

394735-26-3 = 816444-90-3
反应条件:1.1 Reagents: Tert-Butyl Isocyanate,Hydrochloric Acid Solvents: Water; 3 H,25 °C1.2 Reagents: Lithium Hydroxide Solvents: Tetrahydrofuran,Water; 3 H,25 °C
标题:Synthesis And Process Optimization Of Boceprevir: A Protease Inhibitor Drug
作者:Bhalerao,Dinesh S.; Et Al
参考文献:Organic Process Research & Development 日期:2015 卷标:19(11) 页码:1559-1567]

20859-02-3 + 530-62-1 + 75-64-9 = 816444-90-3
反应条件:1.1 Solvents: Toluene; 0 - 5 °C; 2 - 3 H,0 - 5 °C1.2 Reagents: Sodium Hydroxide Solvents: Water; Ph 10 - 11,5 - 10 °C; 10 °C -> 30 °C; 10 - 12 H,25 - 30 °C1.3 Reagents: Hydrochloric Acid Solvents: Water; Ph 1 - 2,0 - 10 °C; 3 - 4 H,25 - 30 °C2.1 Reagents: 4-Methylmorpholine,1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Solvents: Dimethylformamide,Toluene; 0 - 10 °C
标题:Synthesis And Process Optimization Of Boceprevir: A Protease Inhibitor Drug
作者:Bhalerao,Dinesh S.; Et Al
参考文献:Organic Process Research & Development 日期:2015 卷标:19(11) 页码:1559-1567]

394735-26-3 = 816444-90-3
反应条件:1.1 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane; 3 H,Rt2.1 Solvents: Dichloromethane; Rt -> -78 °C; Overnight,Rt3.1 Reagents: Lithium Hydroxide Solvents: Tetrahydrofuran,Water; 3 H,Rt3.2 Reagents: Hydrochloric Acid Solvents: Water; Acidified
标题:Discovery Of (1R,5S)-N-[3-Amino-1-(Cyclobutylmethyl)-2,3-Dioxopropyl]- 3-[2(S)-[[[(1,1-Dimethylethyl)Amino]Carbonyl]Amino]-3,3-Dimethyl-1-Oxobutyl]- 6,6-Dimethyl-3-Azabicyclo[3.1.0]Hexan-2(S)-Carboxamide (Sch 503034),A Selective,Potent,Orally Bioavailable Hepatitis C Virus Ns3 Protease Inhibitor: A Potential Therapeutic Agent For The Treatment Of Hepatitis C Infection
作者:Venkatraman,Srikanth; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2006 卷标:49(20) 页码:6074-6086]

24424-99-5 + 1530-33-2 + 134107-65-6 = 816444-90-3
反应条件:1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran; -78 °C -> Rt1.2 Reagents: Lithium Aluminum Hydride Solvents: Tetrahydrofuran; Reflux1.3 Reagents: Hydrogen Catalysts: Palladium2.1 Solvents: Acetone; 3 H,-5 °C2.2 Solvents: Methanol,Toluene2.3 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane3.1 Reagents: 4-Methylmorpholine,Bop Reagent Solvents: Dimethylformamide,Dichloromethane; Rt -> 0 °C; 24 H,Rt4.1 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane; 3 H,Rt5.1 Solvents: Dichloromethane; Rt -> -78 °C; Overnight,Rt6.1 Reagents: Lithium Hydroxide Solvents: Tetrahydrofuran,Water; 3 H,Rt6.2 Reagents: Hydrochloric Acid Solvents: Water; Acidified
标题:Discovery Of (1R,5S)-N-[3-Amino-1-(Cyclobutylmethyl)-2,3-Dioxopropyl]- 3-[2(S)-[[[(1,1-Dimethylethyl)Amino]Carbonyl]Amino]-3,3-Dimethyl-1-Oxobutyl]- 6,6-Dimethyl-3-Azabicyclo[3.1.0]Hexan-2(S)-Carboxamide (Sch 503034),A Selective,Potent,Orally Bioavailable Hepatitis C Virus Ns3 Protease Inhibitor: A Potential Therapeutic Agent For The Treatment Of Hepatitis C Infection
作者:Venkatraman,Srikanth; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2006 卷标:49(20) 页码:6074-6086]

394735-26-3 = 816444-90-3
反应条件:1.1 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane1.2 Reagents: Triethylamine Solvents: 1,4-Dioxane,Heptane1.3 Reagents: Lithium Hydroxide Solvents: Tetrahydrofuran,Water
标题:Design And Synthesis Of Deuterated Boceprevir Analogs With Enhanced Pharmacokinetic Properties
作者:Morgan,Adam J.; Et Al
参考文献:Journal Of Labelled Compounds And Radiopharmaceuticals 日期:2011 卷标:54(9) 页码:613-624]

62965-35-9 + 565456-77-1 = 816444-90-3
反应条件:1.1 Reagents: 4-Methylmorpholine,Dicyclohexylcarbodiimide,Bop Reagent Solvents: Dimethylformamide; 24 H,25 °C2.1 Reagents: Tert-Butyl Isocyanate,Hydrochloric Acid Solvents: Water; 3 H,25 °C2.2 Reagents: Lithium Hydroxide Solvents: Tetrahydrofuran,Water; 3 H,25 °C
标题:Synthesis And Process Optimization Of Boceprevir: A Protease Inhibitor Drug
作者:Bhalerao,Dinesh S.; Et Al
参考文献:Organic Process Research & Development 日期:2015 卷标:19(11) 页码:1559-1567]

62965-35-9 + 565456-77-1 = 816444-90-3
反应条件:1.1 Reagents: 4-Methylmorpholine,Bop Reagent Solvents: Dimethylformamide,Dichloromethane2.1 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane2.2 Reagents: Triethylamine Solvents: 1,4-Dioxane,Heptane2.3 Reagents: Lithium Hydroxide Solvents: Tetrahydrofuran,Water
标题:Design And Synthesis Of Deuterated Boceprevir Analogs With Enhanced Pharmacokinetic Properties
作者:Morgan,Adam J.; Et Al
参考文献:Journal Of Labelled Compounds And Radiopharmaceuticals 日期:2011 卷标:54(9) 页码:613-624]

219754-00-4 + 18107-18-1 = 816444-90-3
反应条件:1.1 Solvents: Acetone; 3 H,-5 °C1.2 Solvents: Methanol,Toluene1.3 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane2.1 Reagents: 4-Methylmorpholine,Bop Reagent Solvents: Dimethylformamide,Dichloromethane; Rt -> 0 °C; 24 H,Rt3.1 Reagents: Hydrochloric Acid Solvents: 1,4-Dioxane; 3 H,Rt4.1 Solvents: Dichloromethane; Rt -> -78 °C; Overnight,Rt5.1 Reagents: Lithium Hydroxide Solvents: Tetrahydrofuran,Water; 3 H,Rt5.2 Reagents: Hydrochloric Acid Solvents: Water; Acidified
标题:Discovery Of (1R,5S)-N-[3-Amino-1-(Cyclobutylmethyl)-2,3-Dioxopropyl]- 3-[2(S)-[[[(1,1-Dimethylethyl)Amino]Carbonyl]Amino]-3,3-Dimethyl-1-Oxobutyl]- 6,6-Dimethyl-3-Azabicyclo[3.1.0]Hexan-2(S)-Carboxamide (Sch 503034),A Selective,Potent,Orally Bioavailable Hepatitis C Virus Ns3 Protease Inhibitor: A Potential Therapeutic Agent For The Treatment Of Hepatitis C Infection
作者:Venkatraman,Srikanth; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2006 卷标:49(20) 页码:6074-6086

📜N-Boc-L-叔亮氨酸置于n-甲基吗啉,盐酸,(Benzotriazo-1-Yloxy)Tris(Dimethylamino)Phosphonium Hexafluorophosphate,三乙胺,Lithium Hydroxide体系中,用四氢呋喃,1,4-二氧六环,二氯甲烷,水,N,N-二甲基甲酰胺作为反应溶剂,化学反应生成 (1R,2S,5S)-3-[(2S)-2-[[[(叔丁基)氨基]羰基]氨基]-3,3-二甲基-1-氧代丁基]-6,6-二甲基-3-氮杂双环[3.1.0]己烷-2-羧酸
参考文献:Design And Synthesis Of Deuterated Boceprevir Analogs With Enhanced Pharmacokinetic Properties
标题:Design And Synthesis Of Deuterated Boceprevir Analogs With Enhanced Pharmacokinetic Properties
摘要:作为将氘代化学实体平台(dce Platform™)应用于临床验证药物的持续努力的一部分,合成了丙型肝炎病毒蛋白酶抑制剂博切瑞韦的氘代类似物.设计的合成路线允许高水平的同位素纯度进行位点选择性氘掺入.将dce平台™应用于博切瑞韦,使得能够识别出几种显示出显著体外代谢稳定性的氘代类似物.尤其值得注意的是,类似物1G在人体肝微粒体试验中表现出体外半衰期几乎翻倍.本文中详细描述了博切瑞韦同位素类的收敛合成路线及其代谢稳定性测试的结果.
DOI:10.1002/jlcr.1905