tert-butyl N⁵-benzyloxy-N⁵-[(benzyloxy)carbonyl]-N²-(4-methylbenzoyl)-L-glutaminate

Base Information

• Chemical Name: tert-butyl N⁵-benzyloxy-N⁵-[(benzyloxy)carbonyl]-N²-(4-methylbenzoyl)-L-glutaminate
• CAS No.: 861819-85-4
• Molecular Formula: C₃₂H₃₆N₂O₇
• Molecular Weight: 560.647

Synonyms:tert-butyl N⁵-benzyloxy-N⁵-[(benzyloxy)carbonyl]-N²-(4-methylbenzoyl)-L-glutaminate

Chemical Property of tert-butyl N⁵-benzyloxy-N⁵-[(benzyloxy)carbonyl]-N²-(4-methylbenzoyl)-L-glutaminate

Chemical Property:

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Technology Process of tert-butyl N⁵-benzyloxy-N⁵-[(benzyloxy)carbonyl]-N²-(4-methylbenzoyl)-L-glutaminate

There total 6 articles about tert-butyl N⁵-benzyloxy-N⁵-[(benzyloxy)carbonyl]-N²-(4-methylbenzoyl)-L-glutaminate 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: 88.0%

1-tert-butyl N-(4-methylbenzoyl)-L-glutamate (223467-29-6) + N-benzyloxycarbonyl-O-benzylhydroxylamine (15255-86-4) → tert-butyl N5-benzyloxy-N5-[(benzyloxy)carbonyl]-N2-(4-methylbenzoyl)-L-glutaminate (861819-85-4)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1016/j.bmc.2005.04.051

Reference yield:

5-benzyl 1-tert-butyl N-(4-methylbenzoyl)-L-glutamate (223467-27-4) → tert-butyl N5-benzyloxy-N5-[(benzyloxy)carbonyl]-N2-(4-methylbenzoyl)-L-glutaminate (861819-85-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / H₂ / Pd-C / ethanol / 20 °C / atmospheric pressure

2: 88 percent / 4-(dimethylamino)pyridine; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide / 16 h / 20 °C

With dmap; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.04.051

Reference yield:

4-methyl-benzoyl chloride (874-60-2) → tert-butyl N5-benzyloxy-N5-[(benzyloxy)carbonyl]-N2-(4-methylbenzoyl)-L-glutaminate (861819-85-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / N,N-diisopropylethylamine / CHCl₃ / 1 h / 20 °C

2: 76 percent / H₂ / Pd-C / ethanol / 20 °C / atmospheric pressure

3: 88 percent / 4-(dimethylamino)pyridine; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide*HCl / dimethylformamide / 16 h / 20 °C

With dmap; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In ethanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.04.051

upstream raw materials:

1-tert-butyl N-(4-methylbenzoyl)-L-glutamate

N-benzyloxycarbonyl-O-benzylhydroxylamine

5-benzyl 1-tert-butyl N-(4-methylbenzoyl)-L-glutamate

O-benzylhydoxylamine hydrochloride

Downstream raw materials:

N⁵-benzyloxy-N¹-(4-hydroxybutyl)-N²-(4-methylbenzoyl)-L-glutamamide

N⁵-benzyloxy-N⁵-[(benzyloxy)carbonyl]-N²-(4-methylbenzoyl)-L-glutamine

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