(S)-(4-Nitro-benzenesulfonylamino)-phenyl-acetic acid cyclopentyl ester → (S)-(4-Amino-benzenesulfonylamino)-phenyl-acetic acid cyclopentyl ester

HRID 2360626Notes

Reaction equation

HRID 2360626 reaction equation
[CH:1]1([O:6][C:7](=[O:28])[C@@H:8]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[CH:1]1([O:6][C:7](=[O:28])[C@@H:8]([NH:15][S:16]([C:19]2[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=2)(=[O:17])=[O:18])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 57971706(S)-(4-Nitro-benzenesulfonylamino)-phenyl-acetic acid cyclopentyl ester

Product 1

HCID 57971606(S)-(4-Amino-benzenesulfonylamino)-phenyl-acetic acid cyclopentyl esterYield 92.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (S)-(4-Nitro-benzenesulfonylamino)-phenyl-acetic acid cyclopentyl ester (5.29 g, 13.1 mmol) and 10% Pd/C (5.0 g) in EtOAc (350 ml) was hydrogenated under balloon pressure at room temperature for 24 h. The Pd/C catalyst was filtered off through a pad of celite. The filtrate was concentrated under reduced pressure to yield the required product (4.54 g, 92% yield). LCMS purity 100%, m/z 375 [M++H]+.

Workup

  1. filtrationThe Pd/C catalyst was filtered off through a pad of celite
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2ffda14313cc446da985435957583e1f
Source dataset
uspto-grants-2014_04
Patent number
US08686032B2

Reaction notes

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