Water → t-Butyl 2-(4,5-diamino-2-(4-methanesulfonyl-phenoxy)phenyl)-pyrrolidine-1-carboxylate

HRID 13343Notes

Reaction equation

O.[NH2:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][C:6]([C:12]2[N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:14]=[CH:15][CH:16]=2)=[C:5]([O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)[CH:4]=1>[Pt].[C].CC(O)C>[NH2:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:5]([O:24][C:25]2[CH:26]=[CH:27][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:29][CH:30]=2)[CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

20 ml of water and 4 g of 5% platinum-carbon catalyst were added to a 2-propanol (200 ml) solution of 12 g of t-butyl 2-(4-amino-2-(4-methanesulfonyl-phenoxy)-5-nitro-phenyl)-pyrrole-1-carboxylate, and the reaction liquid was stirred under a hydrogen atmosphere of 50 kgf/cm2 at 70° C. for 2 days. The catalyst was removed through filtration through Celite, the solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1) to obtain the entitled compound as a dark brown oily substance.

Workup

customthe reaction liquid
customThe catalyst was removed through filtration through Celite
customthe solvent was evaporated away under reduced pressure
customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1)
customto obtain the entitled compound as a dark brown oily substance

Sources & evidence

ORD record: ord-3a729cc051b54f05acc105f955972771
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728025B2

Reaction notes

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