Water → 4-Chloromethyl-benzoic acid 4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl ester
Reaction equation
[CH2:1]([C@H:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:10][C@H:9]1[OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[Cl:34][CH2:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=1.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:40](=[O:41])[C:39]3[CH:43]=[CH:44][C:36]([CH2:35][Cl:34])=[CH:37][CH:38]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:10][CH:9]1[OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 500 mg (1.33 mmol) (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenol in 10 ml CH2Cl2 were added 20 mg (0.16 mmol) DMAP and 162 mg (1.60 mmol) Et3N and 302 mg (1.60 mmol) 4-chlormethylbenzoylchloride. After 1 hour water was added and the aequous phase was extracted with methylenechloride (3×20 ml). The combined organic layers were dried over MgSO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by chromatography over silica gel to give 280 mg (0.53 mmol, 40%) 4-chloromethyl-benzoic acid 4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl ester as colorless foam.
Workup
- extractionthe aequous phase was extracted with methylenechloride (3×20 ml)
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- customthe solvent was removed under reduced pressure
- customThe crude product was purified by chromatography over silica gel
Sources & evidence
- ORD record
- ord-10b3c9e65a3140b49162c5c8369eb99d
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06407235B1
Reaction notes
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