methyl (S)-2-{(S)-6-azido-2-[(tert-butoxycarbonyl)amino]hexanamido}-3-phenylpropanoate

Base Information

• Chemical Name: methyl (S)-2-{(S)-6-azido-2-[(tert-butoxycarbonyl)amino]hexanamido}-3-phenylpropanoate
• CAS No.: 1414357-73-5
• Molecular Formula: C₂₁H₃₁N₅O₅
• Molecular Weight: 433.508

Synonyms:methyl (S)-2-{(S)-6-azido-2-[(tert-butoxycarbonyl)amino]hexanamido}-3-phenylpropanoate

Chemical Property of methyl (S)-2-{(S)-6-azido-2-[(tert-butoxycarbonyl)amino]hexanamido}-3-phenylpropanoate

Chemical Property:

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Technology Process of methyl (S)-2-{(S)-6-azido-2-[(tert-butoxycarbonyl)amino]hexanamido}-3-phenylpropanoate

There total 2 articles about methyl (S)-2-{(S)-6-azido-2-[(tert-butoxycarbonyl)amino]hexanamido}-3-phenylpropanoate 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: 73.0%

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) + dicyclohexylammonium N-tert-butyloxycarbonyl-2-amino-6-azidohexanoate (846549-33-5) → methyl (S)-2-{(S)-6-azido-2-[(tert-butoxycarbonyl)amino]hexanamido}-3-phenylpropanoate (1414357-73-5)

Guidance literature:

With 1,2,3-Benzotriazole; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In acetonitrile; at 0 - 20 ℃;

DOI:10.1055/s-0032-1316702

Reference yield:

Boc-Lys-OH (13734-28-6) → methyl (S)-2-{(S)-6-azido-2-[(tert-butoxycarbonyl)amino]hexanamido}-3-phenylpropanoate (1414357-73-5)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; benzotriazol-1-yl-sulfonyl azide / water; acetonitrile / 6 h / 20 °C

2: N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 1,2,3-Benzotriazole / acetonitrile / 0 - 20 °C

With 1,2,3-Benzotriazole; benzotriazol-1-yl-sulfonyl azide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In water; acetonitrile;

DOI:10.1055/s-0032-1316702

Reference yield: 100.0%

methyl (S)-2-{(S)-6-azido-2-[(tert-butoxycarbonyl)amino]hexanamido}-3-phenylpropanoate (1414357-73-5) → methyl (S)-2-[(S)-2-amino-6-azidohexanamido]-3-phenylpropanoate hydrochloride (1414357-76-8)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 2h;

DOI:10.1055/s-0032-1316702

upstream raw materials:

Boc-Lys-OH

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

dicyclohexylammonium N-tert-butyloxycarbonyl-2-amino-6-azidohexanoate

Downstream raw materials:

methyl (S)-2-[(S)-2-amino-6-azidohexanamido]-3-phenylpropanoate hydrochloride

methyl (2S,5S,8S)-5-(4-azidobutyl)-2-benzyl-8-[(tert-butoxycarbonyl)amino]-10-methyl-4,7-dioxo-3,6-diazaundecanoate

methyl (S)-2-{(S)-2-[(S)-2-amino-4-methylpentanamido]-6-azidohexanamido}-3-phenylpropanoate hydrochloride

methyl (2S,5S,8S,11S)-5-(4-azidobutyl)-2-benzyl-11-[(tert-butoxycarbonyl)amino]-8-isobutyl-12-methyl-4,7,10-trioxo-3,6,9-triazatridecanoate

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