Water → HCID 67266687, compound

HRID 602750Notes

Reaction equation

HRID 602750 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6]1.[H-].[Na+].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:33])(=O)=O)=CC=1.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:20])[C:4]([S:11]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:12])=[O:13])([F:33])[CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 588007N-FluorobenzenesulfonimideHCID 67266731Benzenesulfonyl-(3-oxo-cyclopentyl)-acetic acid methyl ester

Product 1

HCID 67266687HCID 67266687, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1.34 g (4.5 mmol) of benzenesulfonyl-(3-oxo-cyclopentyl)-acetic acid methyl ester in 15 mL of DMF at 0° C., 199 mg (5.0 mmol, 1.1 eq) of NaH (60%) were added. The reaction mixture was stirred at this temperature for one hour, and 2.14 g (6.75 mmol, 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 (from 2:1 to 2:1) yielding 0.40 g (28%) of (RS,SR)-benzenesulfonyl-fluoro-(3-oxo-cyclopentyl)-acetic acid methyl ester as a white solid, MS: 332 (MNH4+) and 0.52 g (37%) of (RR,SS)-benzenesulfonyl-fluoro-(3-oxo-cyclopentyl)-acetic acid methyl ester as a white solid, MS: 332 (MNH4+).

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 (from 2:1 to 2:1)

Sources & evidence

ORD record
ord-6b196a7d36524c328ec5ab1b9c6d5ff8
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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