2-[2-tert-butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexanoylamino]-3-hydroxy-propionic acid methyl ester

Base Information

• Chemical Name: 2-[2-tert-butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexanoylamino]-3-hydroxy-propionic acid methyl ester
• CAS No.: 916138-34-6
• Molecular Formula: C₂₃H₃₄ClN₃O₈
• Molecular Weight: 515.991
• Mol file: 916138-34-6.mol

Synonyms:2-[2-tert-butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexanoylamino]-3-hydroxy-propionic acid methyl ester

Chemical Property of 2-[2-tert-butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexanoylamino]-3-hydroxy-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[2-tert-butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexanoylamino]-3-hydroxy-propionic acid methyl ester

There total 1 articles about 2-[2-tert-butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexanoylamino]-3-hydroxy-propionic acid methyl 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:

(S)-serine methyl ester (2788-84-3) + N6-[[(2-Chlorophenyl)methoxy]carbonyl]-N2-[t-butyloxycarbonyl]-D-lysine (57096-11-4) → 2-[2-tert-butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexanoylamino]-3-hydroxy-propionic acid methyl ester (916138-34-6)

Guidance literature:

With triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/ja064713e

Reference yield:

2-[2-tert-butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexanoylamino]-3-hydroxy-propionic acid methyl ester (916138-34-6) → 2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]-4,5-dihydrooxazole-4-carboxylic acid methyl ester (916138-35-7)

Guidance literature:

2-[2-tert-butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexanoylamino]-3-hydroxy-propionic acid methyl ester; With 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; at -78 ℃; for 1h;

With potassium carbonate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ja064713e

Reference yield:

2-[2-tert-butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexanoylamino]-3-hydroxy-propionic acid methyl ester (916138-34-6) → 2-[1-({2-[1-({2-[1-amino-5-(2-chloro-benzyloxycarbonylamino)-pentyl]-oxazole-4-carbonyl}-amino)-5-(2-chloro-benzyloxycarbonylamino)-pentyl]-oxazole-4-carbonyl}-amino)-5-(2-chloro-benzyloxycarbonylamino)-pentyl]-oxazole-4-carboxylic acid

Guidance literature:

Multi-step reaction with 6 steps

1.1: DAST / CH₂Cl₂ / 1 h / -78 °C

1.2: K₂CO₃ / CH₂Cl₂ / 1 h / 20 °C

2.1: DBU; BrCCl₃ / CH₂Cl₂ / 0 - 20 °C

3.1: aq. NaOH / methanol / 1 h / 0 °C

4.1: EDC; HOBt; 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

5.1: aq. NaOH / methanol / 1 h / 0 °C

6.1: TFA / CH₂Cl₂ / 1 h

With 2,6-dimethylpyridine; sodium hydroxide; Bromotrichloromethane; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-diaminostilbene-2,2'-disulfonic acid; trifluoroacetic acid; In methanol; dichloromethane;

DOI:10.1021/ja064713e

upstream raw materials:

(S)-serine methyl ester

N6-[[(2-Chlorophenyl)methoxy]carbonyl]-N2-[t-butyloxycarbonyl]-D-lysine

Downstream raw materials:

2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]-4,5-dihydrooxazole-4-carboxylic acid methyl ester

2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]oxazole-4-carboxylic acid methyl ester

2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]oxazole-4-carboxylic acid

C₅₁H₅₄Cl₃N₉O₁₂