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

HRID 13343
Notes
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Reaction equation

HRID 13343 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 962WaterHCID 23145143t-Butyl 2-(4-amino-2-(4-methanesulfonyl-phenoxy)-5-nitro-phenyl)-pyrrole-1-carboxylate

Product 1

HCID 23145168t-Butyl 2-(4,5-diamino-2-(4-methanesulfonyl-phenoxy)phenyl)-pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 178503042HCID 178503042, compoundCatalystHCID 3776Isopropanol
Solvent

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

  1. customthe reaction liquid
  2. customThe catalyst was removed through filtration through Celite
  3. customthe solvent was evaporated away under reduced pressure
  4. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1)
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes