Water → N-(4-Bromo-butyl)-2-(4-fluoro-benzenesulfonyl)-N-trityloxy-acetamide

HRID 1716320Notes

Reaction equation

HRID 1716320 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([O:18][C:19]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:7](=[O:17])[CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1.C1C=C(Cl)C=C(C(OO)=[O:46])C=1.[OH2:49]>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([O:18][C:19]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:7](=[O:17])[CH2:8][S:9]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)(=[O:46])=[O:49]

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 86619940N-(4-Bromo-butyl)-2-(4-fluoro-phenylsulfanyl)-N-trityloxy-acetamide

Product 1

HCID 86619941N-(4-Bromo-butyl)-2-(4-fluoro-benzenesulfonyl)-N-trityloxy-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(4-Bromo-butyl)-2-(4-fluoro-phenylsulfanyl)-N-trityloxy-acetamide from step D (105.2 mg, 0.182 mmol) and mCPBA (max. 77%, 0.21 g) in CH2Cl2 was stirred at room temperature for 30 min. The reaction was diluted with CH2Cl2 and water. The organic layer was sequentially washed with saturated Na2CO3 solution, 10% aqueous Na2SO3 and saturated Na2CO3 solution again. The organic phase was then dried and concentrated under the reduced pressure and purified by a column chromatography (0˜30% EtOAc in hexane). MS: 632.0, (M+Na)+.

Workup

  1. washThe organic layer was sequentially washed with saturated Na2CO3 solution, 10% aqueous Na2SO3 and saturated Na2CO3 solution again
  2. customThe organic phase was then dried
  3. concentrationconcentrated under the reduced pressure
  4. custompurified by a column chromatography (0˜30% EtOAc in hexane)

Sources & evidence

ORD record
ord-b058ba553a584688b7471061afec3f45
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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