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

Base Information

• Chemical Name: 4-{(S)-2-Benzyloxycarbonylamino-2-[(S)-1-((S)-1-carbamoyl-pentyloxymethyl)-3-methyl-butylcarbamoyl]-ethyl}-imidazole-1-carboxylic acid benzyl ester
• CAS No.: 200949-67-3
• Molecular Formula: C₃₄H₄₅N₅O₇
• Molecular Weight: 635.761

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 4-{(S)-2-Benzyloxycarbonylamino-2-[(S)-1-((S)-1-carbamoyl-pentyloxymethyl)-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:

D-norleucine (327-56-0) → 4-{(S)-2-Benzyloxycarbonylamino-2-[(S)-1-((S)-1-carbamoyl-pentyloxymethyl)-3-methyl-butylcarbamoyl]-ethyl}-imidazole-1-carboxylic acid benzyl ester (200949-67-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / 2.5 N aq. H₂SO₄, NaNO₂, KBr / 1.) 0 deg C, 2 h, 2.) room temp., 2 h

2: 1.) HOSu, DCC, 2.) DIEA / 1.) DME, 0 deg C, 2 h, 2.) DME, 3 h

3: 74 percent / NaH / 1,2-dimethoxy-ethane / 1.) -15 deg C, 1 h, 2.) room temp., 2 h

4: DMAP / acetonitrile / 12 h / Ambient temperature

5: 98 percent / 2 N NaOH / tetrahydrofuran / 4 h / Ambient temperature

6: 83 percent / isobutyl chloroformate, N-methylmorpholine, NH₄OH

7: 1.) CF₃COOH, 2.) BOP, N-methylmorpholine

With 4-methyl-morpholine; dmap; ammonium hydroxide; sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; sulfuric acid; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; potassium bromide; sodium nitrite; isobutyl chloroformate; In tetrahydrofuran; 1,2-dimethoxyethane; acetonitrile;

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

Reference yield:

(R)-(+)-2-bromohexanoic acid (616-05-7,2681-83-6,91423-84-6,91423-83-5) → 4-{(S)-2-Benzyloxycarbonylamino-2-[(S)-1-((S)-1-carbamoyl-pentyloxymethyl)-3-methyl-butylcarbamoyl]-ethyl}-imidazole-1-carboxylic acid benzyl ester (200949-67-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) HOSu, DCC, 2.) DIEA / 1.) DME, 0 deg C, 2 h, 2.) DME, 3 h

2: 74 percent / NaH / 1,2-dimethoxy-ethane / 1.) -15 deg C, 1 h, 2.) room temp., 2 h

3: DMAP / acetonitrile / 12 h / Ambient temperature

4: 98 percent / 2 N NaOH / tetrahydrofuran / 4 h / Ambient temperature

5: 83 percent / isobutyl chloroformate, N-methylmorpholine, NH₄OH

6: 1.) CF₃COOH, 2.) BOP, N-methylmorpholine

With 4-methyl-morpholine; dmap; ammonium hydroxide; sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; isobutyl chloroformate; In tetrahydrofuran; 1,2-dimethoxyethane; acetonitrile;

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

Reference yield:

(R)-2-Bromo-hexanoic acid ((S)-1-hydroxymethyl-3-methyl-butyl)-amide (200949-63-9) → 4-{(S)-2-Benzyloxycarbonylamino-2-[(S)-1-((S)-1-carbamoyl-pentyloxymethyl)-3-methyl-butylcarbamoyl]-ethyl}-imidazole-1-carboxylic acid benzyl ester (200949-67-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 74 percent / NaH / 1,2-dimethoxy-ethane / 1.) -15 deg C, 1 h, 2.) room temp., 2 h

2: DMAP / acetonitrile / 12 h / Ambient temperature

3: 98 percent / 2 N NaOH / tetrahydrofuran / 4 h / Ambient temperature

4: 83 percent / isobutyl chloroformate, N-methylmorpholine, NH₄OH

5: 1.) CF₃COOH, 2.) BOP, N-methylmorpholine

With 4-methyl-morpholine; dmap; ammonium hydroxide; sodium hydroxide; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; trifluoroacetic acid; isobutyl chloroformate; In tetrahydrofuran; 1,2-dimethoxyethane; acetonitrile;

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

upstream raw materials:

[(S)-1-((S)-1-Carbamoyl-pentyloxymethyl)-3-methyl-butyl]-carbamic acid tert-butyl ester

Z-His(imZ)-OH

D-norleucine

(R)-(+)-2-bromohexanoic acid

Downstream raw materials:

Boc-D-Phe-Gln-Trp-Ala-Val-Gly-His-LeuΨ(CH2O)Nle-NH2

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