Water → HCID 67266827, compound

HRID 602745Notes

Reaction equation

HRID 602745 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH2:6]1.[H-].[Na+].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:34])(=O)=O)=CC=1.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:21])[C:4]([S:12]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:13])=[O:14])([F:34])[CH:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 588007N-FluorobenzenesulfonimideHCID 11088194Benzenesulfonyl-(3-oxo-cyclohexyl)-acetic acid methyl ester

Product 1

HCID 67266827HCID 67266827, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 10 g (0.032 mol) of benzenesulfonyl-(3-oxo-cyclohexyl)-acetic acid methyl ester in 110 mL of DMF at 0° C., 1.42 g (0.035 mol, 1.1 eq) of NaH (60%) were added. The reaction mixture was stirred at this temperature for one hour, and 15.71 g (0.048 mol, 1.5 eq) of N-fluorobenzenesulfonimide were added. After 2 hours at RT, the reaction mixture was poured into water and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. The resulting two diastereomers were separated by column chromatography on silica gel with heptane/EtOAc 2:1, yielding 3.06 g (27%) of (RS,SR)-benzenesulfonyl-fluoro-(3-oxo-cyclohexyl)-acetic acid methyl ester as a white solid, MS: 329 (MH+) and 3.2 g (28%) of (RR,SS)-benzenesulfonyl-fluoro-(3-oxo-cyclohexyl)-acetic acid methyl ester as a white solid, MS: 329 (MH+).

Workup

  1. waitAfter 2 hours at RT
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting two diastereomers were separated by column chromatography on silica gel with heptane/EtOAc 2:1

Sources & evidence

ORD record
ord-8ca6bfc6e5ac4592988b2d1816b7b3e8
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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