Benzoic acid (3S,6R,10S,13R)-3-(5-bromo-1H-indol-3-ylmethyl)-13-tert-butoxycarbonylamino-10-carbamoylmethyl-2,5,9,12-tetraoxo-1,4,8,11-tetraaza-cyclotetradec-6-yl ester

Base Information

• Chemical Name: Benzoic acid (3S,6R,10S,13R)-3-(5-bromo-1H-indol-3-ylmethyl)-13-tert-butoxycarbonylamino-10-carbamoylmethyl-2,5,9,12-tetraoxo-1,4,8,11-tetraaza-cyclotetradec-6-yl ester
• CAS No.: 219325-45-8
• Molecular Formula: C₃₃H₃₈BrN₇O₉
• Molecular Weight: 756.61
• Mol file: 219325-45-8.mol

Synonyms:

Chemical Property of Benzoic acid (3S,6R,10S,13R)-3-(5-bromo-1H-indol-3-ylmethyl)-13-tert-butoxycarbonylamino-10-carbamoylmethyl-2,5,9,12-tetraoxo-1,4,8,11-tetraaza-cyclotetradec-6-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (3S,6R,10S,13R)-3-(5-bromo-1H-indol-3-ylmethyl)-13-tert-butoxycarbonylamino-10-carbamoylmethyl-2,5,9,12-tetraoxo-1,4,8,11-tetraaza-cyclotetradec-6-yl ester

There total 9 articles about Benzoic acid (3S,6R,10S,13R)-3-(5-bromo-1H-indol-3-ylmethyl)-13-tert-butoxycarbonylamino-10-carbamoylmethyl-2,5,9,12-tetraoxo-1,4,8,11-tetraaza-cyclotetradec-6-yl 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:

Benzoic acid (R)-2-[(S)-2-((R)-3-amino-2-tert-butoxycarbonylamino-propionylamino)-3-carbamoyl-propionylamino]-1-[(S)-2-(5-bromo-1H-indol-3-yl)-1-carboxy-ethylcarbamoyl]-ethyl ester → Benzoic acid (3S,6R,10S,13R)-3-(5-bromo-1H-indol-3-ylmethyl)-13-tert-butoxycarbonylamino-10-carbamoylmethyl-2,5,9,12-tetraoxo-1,4,8,11-tetraaza-cyclotetradec-6-yl ester (219325-45-8)

Guidance literature:

With pentafluorophenyl diphenyl-phosphinate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; Yield given;

DOI:10.1016/S0040-4039(98)02016-4

Reference yield:

N-t-butyloxycarbonyl-D-asparagine (7536-55-2,142847-17-4,75647-01-7) → Benzoic acid (3S,6R,10S,13R)-3-(5-bromo-1H-indol-3-ylmethyl)-13-tert-butoxycarbonylamino-10-carbamoylmethyl-2,5,9,12-tetraoxo-1,4,8,11-tetraaza-cyclotetradec-6-yl ester (219325-45-8)

Guidance literature:

Multi-step reaction with 5 steps

1: iodosobenzene diacetate / propan-1-ol; methyl acetate; H₂O / 0 deg C, 1 h; 50 deg C, 2 h

2: acetone; H₂O

3: (1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, 1-hydroxybenzotriazole, N,N-diisopropylethylamine / dimethylformamide

4: TEA / dimethylformamide; CH₂Cl₂ / 2 h

5: N,N-diisopropylethylamine, pentafluorophenyldiphenylphosphinate / dimethylformamide

With [bis(acetoxy)iodo]benzene; TEA; pentafluorophenyl diphenyl-phosphinate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In propan-1-ol; dichloromethane; acetic acid methyl ester; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(98)02016-4

Reference yield:

(R)-2-tert-butoxycarbonyl-3-aminopropionic acid (73259-81-1,113625-76-6,76387-70-7) → Benzoic acid (3S,6R,10S,13R)-3-(5-bromo-1H-indol-3-ylmethyl)-13-tert-butoxycarbonylamino-10-carbamoylmethyl-2,5,9,12-tetraoxo-1,4,8,11-tetraaza-cyclotetradec-6-yl ester (219325-45-8)

Guidance literature:

Multi-step reaction with 4 steps

1: acetone; H₂O

2: (1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate, 1-hydroxybenzotriazole, N,N-diisopropylethylamine / dimethylformamide

3: TEA / dimethylformamide; CH₂Cl₂ / 2 h

4: N,N-diisopropylethylamine, pentafluorophenyldiphenylphosphinate / dimethylformamide

With TEA; pentafluorophenyl diphenyl-phosphinate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(98)02016-4

upstream raw materials:

(R)-2-tert-butoxycarbonyl-3-aminopropionic acid

N-t-butyloxycarbonyl-D-asparagine

(R)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-((tertbutoxycarbonyl)amino)propanoic acid

Benzoic acid (R)-2-((S)-2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-1-carboxy-ethyl ester