(11S,11aS)-8-(2-benzyloxycarbonylethoxy)-11-hydroxy-7-methoxy-5-oxo-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (11S,11aS)-8-(2-benzyloxycarbonylethoxy)-11-hydroxy-7-methoxy-5-oxo-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carboxylic acid tert-butyl ester
• CAS No.: 679005-40-4
• Molecular Formula: C₂₈H₃₄N₂O₈
• Molecular Weight: 526.587
• Mol file: 679005-40-4.mol

Synonyms:(11S,11aS)-8-(2-benzyloxycarbonylethoxy)-11-hydroxy-7-methoxy-5-oxo-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carboxylic acid tert-butyl ester

Chemical Property of (11S,11aS)-8-(2-benzyloxycarbonylethoxy)-11-hydroxy-7-methoxy-5-oxo-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (11S,11aS)-8-(2-benzyloxycarbonylethoxy)-11-hydroxy-7-methoxy-5-oxo-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carboxylic acid tert-butyl ester

There total 11 articles about (11S,11aS)-8-(2-benzyloxycarbonylethoxy)-11-hydroxy-7-methoxy-5-oxo-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carboxylic acid tert-butyl ester 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: 66.0%

3-[5-tert-butoxycarbonylamino-4-((2S)-2-hydroxymethylpyrrolidine-1-carbonyl)-2-methoxyphenoxy]propionic acid benzyl ester (679005-39-1) → (11S,11aS)-8-(2-benzyloxycarbonylethoxy)-11-hydroxy-7-methoxy-5-oxo-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carboxylic acid tert-butyl ester (679005-40-4)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; at -40 ℃;

DOI:10.1016/j.bmcl.2003.12.017

Reference yield:

4-(2-benzyloxycarbonylethoxy)-5-methoxy-2-nitrobenzoic acid (679005-36-8) → (11S,11aS)-8-(2-benzyloxycarbonylethoxy)-11-hydroxy-7-methoxy-5-oxo-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carboxylic acid tert-butyl ester (679005-40-4)

Guidance literature:

Multi-step reaction with 5 steps

1: (COCl)2; DMF / CH₂Cl₂ / 18 h / 20 °C

2: 100 percent / Et₃N / CH₂Cl₂ / -30 - 20 °C

3: SnCl₂*2H₂O / methanol / 6 h / Heating

4: tetrahydrofuran / 18 h / Heating

5: 18 g / 4 Angstroem molecular sieves; pyridinium dichromate / CH₂Cl₂ / 4 h

With dipyridinium dichromate; oxalyl dichloride; 4 A molecular sieve; triethylamine; N,N-dimethyl-formamide; tin(ll) chloride; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm051199z

Reference yield:

3-(4-carboxy-2-methoxy-5-nitrophenoxy)propanoic acid (219562-36-4) → (11S,11aS)-8-(2-benzyloxycarbonylethoxy)-11-hydroxy-7-methoxy-5-oxo-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carboxylic acid tert-butyl ester (679005-40-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 56 percent / 4-toluenesulfonic acid / toluene / 3.5 h / Heating

2: (COCl)2; DMF / CH₂Cl₂ / 18 h / 20 °C

3: 100 percent / Et₃N / CH₂Cl₂ / -30 - 20 °C

4: SnCl₂*2H₂O / methanol / 6 h / Heating

5: tetrahydrofuran / 18 h / Heating

6: 18 g / 4 Angstroem molecular sieves; pyridinium dichromate / CH₂Cl₂ / 4 h

With dipyridinium dichromate; oxalyl dichloride; 4 A molecular sieve; toluene-4-sulfonic acid; triethylamine; N,N-dimethyl-formamide; tin(ll) chloride; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/jm051199z

upstream raw materials:

3-[5-tert-butoxycarbonylamino-4-((2S)-2-hydroxymethylpyrrolidine-1-carbonyl)-2-methoxyphenoxy]propionic acid benzyl ester

di-tert-butyl dicarbonate

(S)-1-Pyrrolidin-2-yl-methanol

3-(4-carboxy-2-methoxy-5-nitrophenoxy)propanoic acid