4-((S)-2-Benzyloxycarbonylamino-2-{(S)-1-[((S)-1-carbamoyl-3-methyl-butylamino)-methyl]-3-methyl-butylcarbamoyl}-ethyl)-imidazole-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: 4-((S)-2-Benzyloxycarbonylamino-2-{(S)-1-[((S)-1-carbamoyl-3-methyl-butylamino)-methyl]-3-methyl-butylcarbamoyl}-ethyl)-imidazole-1-carboxylic acid benzyl ester
• CAS No.: 200949-60-6
• Molecular Formula: C₃₄H₄₆N₆O₆
• Molecular Weight: 634.776

Synonyms:

Chemical Property of 4-((S)-2-Benzyloxycarbonylamino-2-{(S)-1-[((S)-1-carbamoyl-3-methyl-butylamino)-methyl]-3-methyl-butylcarbamoyl}-ethyl)-imidazole-1-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of 4-((S)-2-Benzyloxycarbonylamino-2-{(S)-1-[((S)-1-carbamoyl-3-methyl-butylamino)-methyl]-3-methyl-butylcarbamoyl}-ethyl)-imidazole-1-carboxylic acid benzyl ester

There total 3 articles about 4-((S)-2-Benzyloxycarbonylamino-2-{(S)-1-[((S)-1-carbamoyl-3-methyl-butylamino)-methyl]-3-methyl-butylcarbamoyl}-ethyl)-imidazole-1-carboxylic acid benzyl 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:

N-carbobenzoxy-L-leucinal (70853-26-8,86852-22-4,71413-15-5) → 4-((S)-2-Benzyloxycarbonylamino-2-{(S)-1-[((S)-1-carbamoyl-3-methyl-butylamino)-methyl]-3-methyl-butylcarbamoyl}-ethyl)-imidazole-1-carboxylic acid benzyl ester (200949-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / CF₃COOH, NaBH₃CN / methanol; acetic acid / 2.75 h

2: 1.) H₂, 11 N HCl, 2.) BOP, N-methylmorpholine / 1.) 10percent Pd/C / 1.) DMF, EtOH, H₂O, room temp., 2.) DMF, room temp.

With 4-methyl-morpholine; hydrogenchloride; hydrogen; sodium cyanoborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; trifluoroacetic acid; palladium on activated charcoal; In methanol; acetic acid;

DOI:10.1016/S0223-5234(99)80063-4

Reference yield:

benzyl (S)-[1-(N-methoxy-N-methylamino)-4-methyl-1-oxopentan-2-yl]carbamate (109075-73-2) → 4-((S)-2-Benzyloxycarbonylamino-2-{(S)-1-[((S)-1-carbamoyl-3-methyl-butylamino)-methyl]-3-methyl-butylcarbamoyl}-ethyl)-imidazole-1-carboxylic acid benzyl ester (200949-60-6)

Guidance literature:

Multi-step reaction with 3 steps

1: LiAlH₄ / 1,2-dimethoxy-ethane / 0.75 h

2: 66 percent / CF₃COOH, NaBH₃CN / methanol; acetic acid / 2.75 h

3: 1.) H₂, 11 N HCl, 2.) BOP, N-methylmorpholine / 1.) 10percent Pd/C / 1.) DMF, EtOH, H₂O, room temp., 2.) DMF, room temp.

With 4-methyl-morpholine; hydrogenchloride; lithium aluminium tetrahydride; hydrogen; sodium cyanoborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; trifluoroacetic acid; palladium on activated charcoal; In methanol; 1,2-dimethoxyethane; acetic acid;

DOI:10.1016/S0223-5234(99)80063-4

Reference yield:

{(S)-1-[((S)-1-Carbamoyl-3-methyl-butylamino)-methyl]-3-methyl-butyl}-carbamic acid benzyl ester (152339-29-2) + Z-His(imZ)-OH (35016-67-2) → 4-((S)-2-Benzyloxycarbonylamino-2-{(S)-1-[((S)-1-carbamoyl-3-methyl-butylamino)-methyl]-3-methyl-butylcarbamoyl}-ethyl)-imidazole-1-carboxylic acid benzyl ester (200949-60-6)

Guidance literature:

With 4-methyl-morpholine; hydrogenchloride; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; palladium on activated charcoal; Yield given. Multistep reaction; 1.) DMF, EtOH, H₂O, room temp., 2.) DMF, room temp.;

DOI:10.1016/S0223-5234(99)80063-4

upstream raw materials:

{(S)-1-[((S)-1-Carbamoyl-3-methyl-butylamino)-methyl]-3-methyl-butyl}-carbamic acid benzyl ester

Z-His(imZ)-OH

N-carbobenzoxy-L-leucinal

benzyl (S)-[1-(N-methoxy-N-methylamino)-4-methyl-1-oxopentan-2-yl]carbamate

Downstream raw materials:

Boc-D-Phe-Gln-Trp-Ala-Val-Gly-His-LeuΨ(CH2NH)Leu-NH2

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