Water → HCID 23078886, compound

HRID 2189394Notes

Reaction equation

HRID 2189394 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10](=[O:26])[CH2:11][CH2:12][NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-:25])=[O:24])(=[O:16])=[O:15])[CH2:6][CH2:5]1.N1C=CC=CC=1.[C:33](OC(=O)C)(=[O:35])[CH3:34].O>ClCCl>[C:33]([O:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([C:10](=[O:26])[CH2:11][CH2:12][NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-:25])=[O:24])(=[O:15])=[O:16])[CH2:8][CH2:9]1)(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 23078879HCID 23078879, compound

Product 1

HCID 23078886HCID 23078886, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-hydroxyethyl)-1-[3-(2-nitrobenzenesulfonylamino)propionyl]piperazine (1.15 g) and pyridine (1.47 mL) in dichloromethane (10 mL) was added acetic anhydride (1.72 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with ethylacetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/2-dichloromethane/methanol=10/1) to give the title compound (0.38 g).

Workup

  1. extractionthe resulting mixture was extracted with ethylacetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/2-dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-fd41e27dbfa9478980ee5ef6c9b224cb
Source dataset
uspto-grants-2012_12
Patent number
US08324176B2

Reaction notes

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