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

Base Information

• Chemical Name: 2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]oxazole-4-carboxylic acid
• CAS No.: 916138-26-6
• Molecular Formula: C₂₂H₂₈ClN₃O₇
• Molecular Weight: 481.933
• Mol file: 916138-26-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]oxazole-4-carboxylic acid 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: 98.0%

2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]oxazole-4-carboxylic acid methyl ester (916138-24-4) → 2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]oxazole-4-carboxylic acid (916138-26-6)

Guidance literature:

With sodium hydroxide; In methanol; at 0 ℃; for 1h;

DOI:10.1021/ja064713e

Reference yield:

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 (916138-26-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / DBU; BrCCl₃ / CH₂Cl₂ / 0 - 20 °C

2: 98 percent / aq. NaOH / methanol / 1 h / 0 °C

With sodium hydroxide; Bromotrichloromethane; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane;

DOI:10.1021/ja064713e

Reference yield:

Boc-(S)-Lys(2-Cl-Z)-OH (54613-99-9) → 2-[1-tert-butoxycarbonylamino-5-(2-chlorobenzyloxycarbonylamino)pentyl]oxazole-4-carboxylic acid (916138-26-6)

Guidance literature:

Multi-step reaction with 4 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

3.1: 66 percent / DBU; BrCCl₃ / CH₂Cl₂ / 0 - 20 °C

4.1: 98 percent / aq. NaOH / methanol / 1 h / 0 °C

With sodium hydroxide; Bromotrichloromethane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; 4,4'-diaminostilbene-2,2'-disulfonic acid; In methanol; dichloromethane;

DOI:10.1021/ja064713e

upstream raw materials:

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

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

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

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

Downstream raw materials:

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

C₅₇H₆₆Cl₃N₉O₁₅

C₅₆H₆₄Cl₃N₉O₁₅