Hydrochloric Acid → HCID 54116941, compound

HRID 257331Notes

Reaction equation

HRID 257331 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]([C:14]1([F:20])[CH2:18][CH2:17][CH2:16][CH:15]1[OH:19])=[O:13].Cl>N1C=CC=CC=1>[CH3:10][O:11][C:12]([C:14]1([F:20])[CH2:18][CH2:17][CH2:16][CH:15]1[O:19][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 19783080HCID 19783080, compound

Product 1

HCID 54116941HCID 54116941, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

.045 g (3 mmol) of benzoyl chloride was added under ice cooling to a mixture of 0.5 g (3 mmol) of the 1-fluoro-2-hydroxy-1-cyclopentanecarboxylic acid methyl ester in cis form (compound number 2a) synthesized in Example 1 and 2 ml of pyridine, the temperature of the mixture was brought back to room temperature, and the mixture was stirred for 5 hours. The reaction solution was poured into a diluted aqueous hydrochloric acid solution and extracted with ethyl acetate and the extract was successively washed with saturated saline, a saturated aqueous sodium bicarbonate solution and saturated saline. The ethyl acetate layer was dried over anhydrous magnesium sulfate and the solvent was distilled away to obtain 0.68 g (yield: 84%) of the objective 2-benzoyloxy-1-fluoro-cyclopentanecarboxylic acid methyl ester in cis form (compound number 4a).

Workup

  1. customwas brought back to room temperature
  2. extractionextracted with ethyl acetate
  3. washthe extract was successively washed with saturated saline
  4. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-551d9bbae9e54967b8024222f375619c
Source dataset
uspto-grants-1993_11
Patent number
US05262385

Reaction notes

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