(S)-2-((S)-4-Carbamoyl-2-{[(S)-1-((S)-pyrrolidine-2-carbonyl)-pyrrolidine-2-carbonyl]-amino}-butyrylamino)-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid methyl ester

Base Information

• Chemical Name: (S)-2-((S)-4-Carbamoyl-2-{[(S)-1-((S)-pyrrolidine-2-carbonyl)-pyrrolidine-2-carbonyl]-amino}-butyrylamino)-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid methyl ester
• CAS No.: 73995-32-1
• Molecular Formula: C₃₀H₄₃ClN₆O₈
• Molecular Weight: 651.16

Synonyms:

Chemical Property of (S)-2-((S)-4-Carbamoyl-2-{[(S)-1-((S)-pyrrolidine-2-carbonyl)-pyrrolidine-2-carbonyl]-amino}-butyrylamino)-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid methyl ester

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of (S)-2-((S)-4-Carbamoyl-2-{[(S)-1-((S)-pyrrolidine-2-carbonyl)-pyrrolidine-2-carbonyl]-amino}-butyrylamino)-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid methyl ester

There total 8 articles about (S)-2-((S)-4-Carbamoyl-2-{[(S)-1-((S)-pyrrolidine-2-carbonyl)-pyrrolidine-2-carbonyl]-amino}-butyrylamino)-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid methyl 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:

Boc-Gln-ONp (15387-45-8) → (S)-2-((S)-4-Carbamoyl-2-{[(S)-1-((S)-pyrrolidine-2-carbonyl)-pyrrolidine-2-carbonyl]-amino}-butyrylamino)-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid methyl ester (73995-32-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 83.6 percent / 1.) TEA / dimethylformamide / 24 h / Ambient temperature

2: TFA / 0.67 h / Ambient temperature

3: 1.) TEA / tetrahydrofuran / 72 h / Ambient temperature

4: TFA / 1 h / Ambient temperature

With TEA; trifluoroacetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.53.192

Reference yield:

N-tert-butoxycarbonyl-L-prolyl-L-proline (15401-08-8) → (S)-2-((S)-4-Carbamoyl-2-{[(S)-1-((S)-pyrrolidine-2-carbonyl)-pyrrolidine-2-carbonyl]-amino}-butyrylamino)-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid methyl ester (73995-32-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 71.6 percent / DCC / tetrahydrofuran / 1 h / -20 - -10 °C

2: 1.) TEA / tetrahydrofuran / 72 h / Ambient temperature

3: TFA / 1 h / Ambient temperature

With TEA; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1246/bcsj.53.192

Reference yield:

Nε-(2-Chlorophenylmethoxycarbonyl)-(S)-lysine (42390-97-6,201014-19-9) → (S)-2-((S)-4-Carbamoyl-2-{[(S)-1-((S)-pyrrolidine-2-carbonyl)-pyrrolidine-2-carbonyl]-amino}-butyrylamino)-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid methyl ester (73995-32-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 70.6 percent / thionyl chloride / 72 h / Ambient temperature

2: 83.6 percent / 1.) TEA / dimethylformamide / 24 h / Ambient temperature

3: TFA / 0.67 h / Ambient temperature

4: 1.) TEA / tetrahydrofuran / 72 h / Ambient temperature

5: TFA / 1 h / Ambient temperature

With thionyl chloride; TEA; trifluoroacetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.53.192

upstream raw materials:

Boc-Pro-Pro-Gln-Lys-OMe

Boc-Gln-ONp

N-tert-butoxycarbonyl-L-prolyl-L-proline

N^ε-(2-Chlorophenylmethoxycarbonyl)-(S)-lysine

Downstream raw materials:

Boc-Leu-Glu(OBu^t)-Gly-Pro-Pro-Gln-Lys-OMe

Boc-Leu-Glu(OBu^t)-Gly-Pro-Pro-Gln-Lys-N2H3

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