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

Base Information

• Chemical Name: 4-{(S)-2-Benzyloxycarbonylamino-2-[(S)-1-((S)-1-carbamoylmethyl-3-methyl-butylcarbamoyl)-3-methyl-butylcarbamoyl]-ethyl}-imidazole-1-carboxylic acid benzyl ester
• CAS No.: 200949-21-9
• Molecular Formula: C₃₅H₄₆N₆O₇
• Molecular Weight: 662.786

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

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

There total 4 articles about 4-{(S)-2-Benzyloxycarbonylamino-2-[(S)-1-((S)-1-carbamoylmethyl-3-methyl-butylcarbamoyl)-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: 90.0%

(S)-3-((S)-2-Amino-4-methyl-pentanoylamino)-5-methyl-hexanoic acid amide + Z-His(imZ)-OH (35016-67-2) → 4-{(S)-2-Benzyloxycarbonylamino-2-[(S)-1-((S)-1-carbamoylmethyl-3-methyl-butylcarbamoyl)-3-methyl-butylcarbamoyl]-ethyl}-imidazole-1-carboxylic acid benzyl ester (200949-21-9)

Guidance literature:

With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

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

Reference yield:

Z-Leu-OH (2018-66-8) → 4-{(S)-2-Benzyloxycarbonylamino-2-[(S)-1-((S)-1-carbamoylmethyl-3-methyl-butylcarbamoyl)-3-methyl-butylcarbamoyl]-ethyl}-imidazole-1-carboxylic acid benzyl ester (200949-21-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / HCl, BOP, N-methylmorpholine / dimethylformamide / 2 h / Ambient temperature

2: 98 percent / H₂, 11 N HCl / 10percent Pd/C / dimethylformamide; ethanol; H₂O / 4 h / Ambient temperature

3: 90 percent / BOP, N-methylmorpholine / dimethylformamide / 2 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; palladium on activated charcoal; In ethanol; water; N,N-dimethyl-formamide;

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

Reference yield:

(S)-3-Amino-5-methyl-hexanoic acid amide → 4-{(S)-2-Benzyloxycarbonylamino-2-[(S)-1-((S)-1-carbamoylmethyl-3-methyl-butylcarbamoyl)-3-methyl-butylcarbamoyl]-ethyl}-imidazole-1-carboxylic acid benzyl ester (200949-21-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / HCl, BOP, N-methylmorpholine / dimethylformamide / 2 h / Ambient temperature

2: 98 percent / H₂, 11 N HCl / 10percent Pd/C / dimethylformamide; ethanol; H₂O / 4 h / Ambient temperature

3: 90 percent / BOP, N-methylmorpholine / dimethylformamide / 2 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; palladium on activated charcoal; In ethanol; water; N,N-dimethyl-formamide;

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

upstream raw materials:

Z-His(imZ)-OH

Z-Leu-OH

[(S)-1-((S)-1-Carbamoylmethyl-3-methyl-butylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester

Downstream raw materials:

Boc-D-Phe-Gln-Trp-Ala-Val-Gly-His-Leu-β-homo-Leu-NH2

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