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

Base Information

• Chemical Name: 2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]-4,5-dihydrooxazole-4-carboxylic acid methyl ester
• CAS No.: 916138-23-3
• Molecular Formula: C₂₃H₃₂ClN₃O₇
• Molecular Weight: 497.976
• Mol file: 916138-23-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about 2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]-4,5-dihydrooxazole-4-carboxylic 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: 79.0%

methyl [Nα-(tert-butoxycarbonyl)-Nε-(2-chlorobenzylcarbonyl)-L-lysyl]-L-serinate (251320-34-0) → 2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]-4,5-dihydrooxazole-4-carboxylic acid methyl ester (916138-23-3)

Guidance literature:

methyl [N^α-(tert-butoxycarbonyl)-Nε-(2-chlorobenzylcarbonyl)-L-lysyl]-L-serinate; 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:

Boc-(S)-Lys(2-Cl-Z)-OH (54613-99-9) → 2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]-4,5-dihydrooxazole-4-carboxylic acid methyl ester (916138-23-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / triethylamine; DCC / CH₂Cl₂ / 2 h / 0 °C

2.1: DAST / CH₂Cl₂ / 1 h / -78 °C

2.2: 79 percent / K₂CO₃ / CH₂Cl₂ / 1 h / 20 °C

With triethylamine; dicyclohexyl-carbodiimide; 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane;

DOI:10.1021/ja064713e

Reference yield: 66.0%

2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]-4,5-dihydrooxazole-4-carboxylic acid methyl ester (916138-23-3) → 2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]oxazole-4-carboxylic acid methyl ester (916138-24-4)

Guidance literature:

With Bromotrichloromethane; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ja064713e

upstream raw materials:

methyl [N^α-(tert-butoxycarbonyl)-Nε-(2-chlorobenzylcarbonyl)-L-lysyl]-L-serinate

Boc-(S)-Lys(2-Cl-Z)-OH

Downstream raw materials:

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

2-[1-({2-[1-tert-butoxycarbonylamino-5-(2-chloro-benzyloxycarbonylamino)-pentyl]-oxazole-4-carbonyl}-amino)-5-(2-chloro-benzyloxycarbonylamino)-pentyl]-oxazole-4-carboxylic acid methyl ester

C₅₁H₅₄Cl₃N₉O₁₂