benzoic acid 5-(S)-amino-2-(S)-[(1-(S)-carboxy-cyclohexyl-methyl)-carbamoyl]-4-oxo-6-phenyl-hexyl ester trifluroacetate

Base Information

• Chemical Name: benzoic acid 5-(S)-amino-2-(S)-[(1-(S)-carboxy-cyclohexyl-methyl)-carbamoyl]-4-oxo-6-phenyl-hexyl ester trifluroacetate
• CAS No.: 1322615-58-6
• Molecular Formula: C₂HF₃O₂*C₂₈H₃₄N₂O₆
• Molecular Weight: 608.612

Synonyms:benzoic acid 5-(S)-amino-2-(S)-[(1-(S)-carboxy-cyclohexyl-methyl)-carbamoyl]-4-oxo-6-phenyl-hexyl ester trifluroacetate

Chemical Property of benzoic acid 5-(S)-amino-2-(S)-[(1-(S)-carboxy-cyclohexyl-methyl)-carbamoyl]-4-oxo-6-phenyl-hexyl ester trifluroacetate

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Technology Process of benzoic acid 5-(S)-amino-2-(S)-[(1-(S)-carboxy-cyclohexyl-methyl)-carbamoyl]-4-oxo-6-phenyl-hexyl ester trifluroacetate

There total 6 articles about benzoic acid 5-(S)-amino-2-(S)-[(1-(S)-carboxy-cyclohexyl-methyl)-carbamoyl]-4-oxo-6-phenyl-hexyl ester trifluroacetate 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: 63.0%

benzoic acid 5-(S)-benzyloxycarbonylamino-2-(S)-[(1-(S)-tert-butoxycarbonyl-cyclohexyl-methyl)-carbamoyl]-4-oxo-6-phenyl-hexyl ester (1322615-77-9) + trifluoroacetic acid (76-05-1) → benzoic acid 5-(S)-amino-2-(S)-[(1-(S)-carboxy-cyclohexyl-methyl)-carbamoyl]-4-oxo-6-phenyl-hexyl ester trifluroacetate (1322615-58-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.05.108

Reference yield:

benzoic acid 2-(S)-(4-(R)-benzyl-2-oxo-oxazolidine-3-carbonyl)-5-(S)-benzyloxycarbonyl-4-oxo-6-phenyl-hexyl ester (1322615-30-4) → benzoic acid 5-(S)-amino-2-(S)-[(1-(S)-carboxy-cyclohexyl-methyl)-carbamoyl]-4-oxo-6-phenyl-hexyl ester trifluroacetate (1322615-58-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 0.25 h / -10 °C

2.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.05 h / 20 °C

2.2: 20 °C

3.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / Inert atmosphere

With lithium hydroxide monohydrate; palladium 10% on activated carbon; water; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.05.108

Reference yield:

benzoic acid 2-(S)-(4-(R)-benzyl-2-oxo-oxazolidine-3-carbonyl)-5-(S)-[benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-4-oxo-6-phenyl-hexyl ester (1322615-29-1) → benzoic acid 5-(S)-amino-2-(S)-[(1-(S)-carboxy-cyclohexyl-methyl)-carbamoyl]-4-oxo-6-phenyl-hexyl ester trifluroacetate (1322615-58-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.58 h / 20 °C

2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 0.25 h / -10 °C

3.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.05 h / 20 °C

3.2: 20 °C

4.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / Inert atmosphere

With ammonium cerium (IV) nitrate; lithium hydroxide monohydrate; palladium 10% on activated carbon; water; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmcl.2011.05.108

upstream raw materials:

[1-(S)-benzyl-5-(4-(R)-benzyl-2-oxo-oxazolidin-3-yl)-4-(S)-hydroxymethyl-2,5-dioxo-pentyl]-(4-methoxy-benzyl)-carbamic acid benzyl ester

benzoic acid 2-(S)-(4-(R)-benzyl-2-oxo-oxazolidine-3-carbonyl)-5-(S)-[benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-4-oxo-6-phenyl-hexyl ester

benzoic acid 2-(S)-(4-(R)-benzyl-2-oxo-oxazolidine-3-carbonyl)-5-(S)-benzyloxycarbonyl-4-oxo-6-phenyl-hexyl ester

benzoic acid 5-(S)-benzyloxycarbonylamino-2-(S)-[(1-(S)-tert-butoxycarbonyl-cyclohexyl-methyl)-carbamoyl]-4-oxo-6-phenyl-hexyl ester

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