N-(tert-butoxy)-2-[1-(4-phenoxyphenylthio)cyclopent-1-yl]-acetamide → N-hydroxy-2-[1-(4-phenoxyphenylthio)-cyclopent-1-yl]-acetamide

HRID 1584397Notes

Reaction equation

HRID 1584397 reaction equation
C([O:5][NH:6][C:7](=[O:28])[CH2:8][C:9]1([S:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:17][CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1)(C)(C)C>FC(F)(F)C(O)=O>[OH:5][NH:6][C:7](=[O:28])[CH2:8][C:9]1([S:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:17][CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

3

Reactant 1

HCID 21224113N-(tert-butoxy)-2-[1-(4-phenoxyphenylthio)cyclopent-1-yl]-acetamide

Product 1

HCID 21224318N-hydroxy-2-[1-(4-phenoxyphenylthio)-cyclopent-1-yl]-acetamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The N-tert-butoxy-2-[1-(4-phenoxyphenylthio)-cyclopent-1-yl]-acetamide was dissolved in trifluoroacetic acid (6 ml) and allowed to stand for 24 hours. The acid was evaporated off under reduced pressure and the product purified by preparative TLC, eluting with 6.5% methanol/methylene chloride gave N-hydroxy-2-[1-(4-phenoxyphenylthio)-cyclopent-1-yl]-acetamide (100 mg).

Workup

  1. customThe acid was evaporated off under reduced pressure
  2. customthe product purified by preparative TLC
  3. washeluting with 6.5% methanol/methylene chloride

Sources & evidence

ORD record
ord-ff650d42c7dc4b5b89dc19df337cac31
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

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