(2S)-2-((2S,4R)-4-azido-1-(phenylsulfonyl)pyrrolidine-2-carboxamido)-3-(4-((pyrrolidine-1-carbonyl)oxy)phenyl)propanoic acid

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Chemical Name:(2S)-2-((2S,4R)-4-azido-1-(phenylsulfonyl)pyrrolidine-2-carboxamido)-3-(4-((pyrrolidine-1-carbonyl)oxy)phenyl)propanoic acid
CAS No.:1541175-37-4
Molecular Formula:C₂₅H₂₈N₆O₇S
Molecular Weight:556.599
Hs Code.:

Synonyms:(2S)-2-((2S,4R)-4-azido-1-(phenylsulfonyl)pyrrolidine-2-carboxamido)-3-(4-((pyrrolidine-1-carbonyl)oxy)phenyl)propanoic acid

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Chemical Property of (2S)-2-((2S,4R)-4-azido-1-(phenylsulfonyl)pyrrolidine-2-carboxamido)-3-(4-((pyrrolidine-1-carbonyl)oxy)phenyl)propanoic acid

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Technology Process of (2S)-2-((2S,4R)-4-azido-1-(phenylsulfonyl)pyrrolidine-2-carboxamido)-3-(4-((pyrrolidine-1-carbonyl)oxy)phenyl)propanoic acid

There total 11 articles about (2S)-2-((2S,4R)-4-azido-1-(phenylsulfonyl)pyrrolidine-2-carboxamido)-3-(4-((pyrrolidine-1-carbonyl)oxy)phenyl)propanoic acid 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: 94.0%

: 1541175-33-0
4-((2S)-2-((2S,4R)-4-azido-1-(phenylsulfonyl)pyrrolidine-2-carboxamido)-3-methoxy-3-oxopropyl)phenyl pyrrolidine-1-carboxylate

: 1541175-37-4
(2S)-2-((2S,4R)-4-azido-1-(phenylsulfonyl)pyrrolidine-2-carboxamido)-3-(4-((pyrrolidine-1-carbonyl)oxy)phenyl)propanoic acid

Guidance literature:: 4-((2S)-2-((2S,4R)-4-azido-1-(phenylsulfonyl)pyrrolidine-2-carboxamido)-3-methoxy-3-oxopropyl)phenyl pyrrolidine-1-carboxylate; With sodium hydroxide; In tetrahydrofuran; ethanol; at 20 ℃; for 1h;

With hydrogenchloride; In water;
DOI:10.1039/c3ob42332h

Reference yield:

: 16257-76-4
1-(benzenesulphonyl)-4-hydroxypyrrolidine-2-carboxylic acid

: 1541175-37-4
(2S)-2-((2S,4R)-4-azido-1-(phenylsulfonyl)pyrrolidine-2-carboxamido)-3-(4-((pyrrolidine-1-carbonyl)oxy)phenyl)propanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / dichloromethane / 0 - 20 °C / Inert atmosphere

2: toluene; water / 48 h / 80 °C

3: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

4: sodium azide / dimethyl sulfoxide / 80 °C

5: sodium hydroxide / tetrahydrofuran; ethanol / 1 h / 20 °C

With sodium azide; di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; toluene;
DOI:10.1039/c3ob42332h

Reference yield:

: 13512-31-7
N-(benzyloxycarbonyl)-L-tyrosine methyl ester

: 1541175-37-4
(2S)-2-((2S,4R)-4-azido-1-(phenylsulfonyl)pyrrolidine-2-carboxamido)-3-(4-((pyrrolidine-1-carbonyl)oxy)phenyl)propanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: potassium carbonate / acetonitrile / 0.75 h / 100 °C / Microwave irradiation

2.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h

3.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: sodium hydroxide / tetrahydrofuran; ethanol / 1 h / 20 °C

With palladium 10% on activated carbon; hydrogen; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/c3ob42332h