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Methanol → 1-tert-Butoxycarbonyl-4-[(5-chloroindol-2-yl)sulfonyl]piperazine

HRID 352771
Notes
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Reaction equation

HRID 352771 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[N:18](S(C3C=CC=CC=3)(=O)=O)[C:19]3[C:24]([CH:25]=2)=[CH:23][C:22]([Cl:26])=[CH:21][CH:20]=3)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Na+].[Cl-].[NH4+]>ClCCl.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([S:14]([C:17]2[NH:18][C:19]3[C:24]([CH:25]=2)=[CH:23][C:22]([Cl:26])=[CH:21][CH:20]=3)(=[O:15])=[O:16])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 227103001-tert-Butoxycarbonyl-4-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]piperazine

Product 1

HCID 227107811-tert-Butoxycarbonyl-4-[(5-chloroindol-2-yl)sulfonyl]piperazine

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

To 1-tert-butoxycarbonyl-4-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]piperazine (4.84 g), a 0.5N methanol solution of sodium hydroxide (20 ml) was added, followed by stirring at room temperature for 1 hour. Under ice cooling, a saturated aqueous solution of ammonium chloride was added to the reaction mixture. Water and dichloromethane were then added to separate the organic layer. The organic layer was dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (methanol:dichloromethane=1:20), whereby the title compound (3.33 g, 93%) was obtained as colorless powder.

Workup

  1. customto separate the organic layer
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customThe residue obtained
  4. distillationby distilling off the solvent under reduced pressure
  5. customwas purified by chromatography on a silica gel column (methanol:dichloromethane=1:20), whereby the title compound (3.33 g, 93%)
  6. customwas obtained as colorless powder

Sources & evidence

ORD record
ord-555e734009d5401f85c67d21d1615f52
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06747023B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes