(3RS)-1-(3-azabicyclo[3.2.2]nonan-3-yl)carboxymethyl-3-benzyloxycarbonylamino-5-cyclopropyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one

Base Information

Chemical Name:(3RS)-1-(3-azabicyclo[3.2.2]nonan-3-yl)carboxymethyl-3-benzyloxycarbonylamino-5-cyclopropyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one
CAS No.:205995-97-7
Molecular Formula:C₃₁H₃₆N₄O₄
Molecular Weight:528.651
Hs Code.:

Synonyms:(3RS)-1-(3-azabicyclo[3.2.2]nonan-3-yl)carboxymethyl-3-benzyloxycarbonylamino-5-cyclopropyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one

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Chemical Property of (3RS)-1-(3-azabicyclo[3.2.2]nonan-3-yl)carboxymethyl-3-benzyloxycarbonylamino-5-cyclopropyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one

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Technology Process of (3RS)-1-(3-azabicyclo[3.2.2]nonan-3-yl)carboxymethyl-3-benzyloxycarbonylamino-5-cyclopropyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one

There total 6 articles about (3RS)-1-(3-azabicyclo[3.2.2]nonan-3-yl)carboxymethyl-3-benzyloxycarbonylamino-5-cyclopropyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.6%

: 205995-96-6
(3RS)-3-benzyloxycarbonylamino-1-carboxymethyl-2,3-dihydro-5-cyclopropyl-9-methyl-1H-1,4-benzodiazepin-2-one

: 283-24-9
3-azabicyclo[3,2,2]nonane

: 205995-97-7
(3RS)-1-(3-azabicyclo[3.2.2]nonan-3-yl)carboxymethyl-3-benzyloxycarbonylamino-5-cyclopropyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1248/cpb.48.1

Reference yield:

: 124676-19-3
2-(benzotriazol-1-yl)-N-(benzyloxycarbonyl)glycine

: 205995-97-7
(3RS)-1-(3-azabicyclo[3.2.2]nonan-3-yl)carboxymethyl-3-benzyloxycarbonylamino-5-cyclopropyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: (COCl)2; DMF / tetrahydrofuran / 2 h / 0 °C

2.1: N-methylmorpholine / tetrahydrofuran / 0 - 20 °C

3.1: NH₃ / methanol / 20 °C

4.1: NaH / dimethylformamide / 4 h / 0 - 20 °C

4.2: 100 percent / dimethylformamide / 5.5 h / 20 °C

5.1: 91.6 percent / 1 N aq. NaOH / 1,2-dimethoxy-ethane / 20 °C

6.1: 91.6 percent / N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide*HCl; HOBT; Et₃N / dimethylformamide / 20 °C

With 4-methyl-morpholine; sodium hydroxide; oxalyl dichloride; ammonia; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; N,N-dimethyl-formamide; 1.1: Chlorination / 2.1: Acylation / 3.1: Cyclization / 4.1: deprotonation / 4.2: Alkylation / 5.1: Hydrolysis / 6.1: amidation;
DOI:10.1248/cpb.48.1

Reference yield:

: 517874-18-9
(Benzotriazol-1-yl-chlorocarbonyl-methyl)-carbamic acid benzyl ester

: 205995-97-7
(3RS)-1-(3-azabicyclo[3.2.2]nonan-3-yl)carboxymethyl-3-benzyloxycarbonylamino-5-cyclopropyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: N-methylmorpholine / tetrahydrofuran / 0 - 20 °C

2.1: NH₃ / methanol / 20 °C

3.1: NaH / dimethylformamide / 4 h / 0 - 20 °C

3.2: 100 percent / dimethylformamide / 5.5 h / 20 °C

4.1: 91.6 percent / 1 N aq. NaOH / 1,2-dimethoxy-ethane / 20 °C

5.1: 91.6 percent / N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide*HCl; HOBT; Et₃N / dimethylformamide / 20 °C

With 4-methyl-morpholine; sodium hydroxide; ammonia; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; N,N-dimethyl-formamide; 1.1: Acylation / 2.1: Cyclization / 3.1: deprotonation / 3.2: Alkylation / 4.1: Hydrolysis / 5.1: amidation;
DOI:10.1248/cpb.48.1