methyl (S)-3-(1H-indol-3-yl)-2-[(S)-3-methyl-2-(2-nitrophenylsulfonamido)butanamido]propanoate

Base Information

• Chemical Name: methyl (S)-3-(1H-indol-3-yl)-2-[(S)-3-methyl-2-(2-nitrophenylsulfonamido)butanamido]propanoate
• CAS No.: 1613043-75-6
• Molecular Formula: C₂₃H₂₆N₄O₇S
• Molecular Weight: 502.548

Synonyms:methyl (S)-3-(1H-indol-3-yl)-2-[(S)-3-methyl-2-(2-nitrophenylsulfonamido)butanamido]propanoate

Chemical Property of methyl (S)-3-(1H-indol-3-yl)-2-[(S)-3-methyl-2-(2-nitrophenylsulfonamido)butanamido]propanoate

Chemical Property:

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Technology Process of methyl (S)-3-(1H-indol-3-yl)-2-[(S)-3-methyl-2-(2-nitrophenylsulfonamido)butanamido]propanoate

There total 4 articles about methyl (S)-3-(1H-indol-3-yl)-2-[(S)-3-methyl-2-(2-nitrophenylsulfonamido)butanamido]propanoate 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: 91.0%

L-tryptophan methyl ester (4299-70-1) + (S)-3-methyl-2-(2-nitrophenylsulfonamido)butanoic acid (199783-36-3) → methyl (S)-3-(1H-indol-3-yl)-2-[(S)-3-methyl-2-(2-nitrophenylsulfonamido)butanamido]propanoate (1613043-75-6)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1002/ejoc.201301773

Reference yield:

L-valine tert-butylester hydrochloride (13518-40-6) → methyl (S)-3-(1H-indol-3-yl)-2-[(S)-3-methyl-2-(2-nitrophenylsulfonamido)butanamido]propanoate (1613043-75-6)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 20 h / 20 °C

2: trifluoroacetic acid / dichloromethane / 3 h / 0 °C

3: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / 24 h / 20 °C

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1002/ejoc.201301773

Reference yield:

2-Nitrobenzenesulfonyl chloride (1694-92-4) → methyl (S)-3-(1H-indol-3-yl)-2-[(S)-3-methyl-2-(2-nitrophenylsulfonamido)butanamido]propanoate (1613043-75-6)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 20 h / 20 °C

2: trifluoroacetic acid / dichloromethane / 3 h / 0 °C

3: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane / 24 h / 20 °C

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1002/ejoc.201301773

upstream raw materials:

L-valine tert-butylester hydrochloride

2-Nitrobenzenesulfonyl chloride

tert-butyl (S)-3-methyl-2-(2-nitrophenylsulfonamido)butanoate

L-tryptophan methyl ester

Downstream raw materials:

(S)-3-(1H-indol-3-yl)-2-{(S)-3-isopropyl-4-[(2-nitrophenyl)sulfonyl]-2-oxopiperazin-1-yl} propanoic acid

tert-butyl {(S)-1-{[(S)-1-({(S)-1-[(S)-4-{(S)-1-[(2-amino-2-oxoethyl)amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl}-2-isopropyl-3-oxopiperazin-1-yl]-3-(tert-butoxy)-1-oxopropan-2-yl}amino)-1-oxo-3-phenylpropan-2-yl]amino}-3-[4-(tert-butoxy)phenyl]-1-oxopropan-2-yl}carbamate

(S)-2-amino-N-[(S)-1-({(S)-1-[(S)-4-{(S)-1-[(2-amino-2-oxoethyl)amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl}-2-isopropyl-3-oxopiperazin-1-yl]-3-hydroxy-1-oxopropan-2-yl}amino)-1-oxo-3-phenylpropan-2-yl]-3-(4-hydroxyphenyl)propanamide

methyl (S)-3-(1H-indol-3-yl)-2-{(S)-3-isopropyl-4-[(2-nitrophenyl)sulfonyl]-2-oxopiperazin-1-yl}propanoate

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