HCID 69507873, compound → HCID 10216958, compound

HRID 1767202Notes

Reaction equation

HRID 1767202 reaction equation
C([O:8][C:9](=[O:39])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]2[CH2:20][CH2:19][CH2:18][C:17]=2[C:21]2[CH:26]=[C:25]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:24]=[CH:23][C:22]=2[O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:11]=1)C1C=CC=CC=1>C(O)C.[OH-].[Na+].O>[CH3:30][S:27]([C:25]1[CH:24]=[CH:23][C:22]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[C:21]([C:17]2[CH2:18][CH2:19][CH2:20][C:16]=2[C:12]2[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=2)[C:9]([OH:39])=[O:8])[CH:26]=1)(=[O:28])=[O:29]

Participants

5

Reactant 1

HCID 69507873HCID 69507873, compound

Product 1

HCID 10216958HCID 10216958, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-{2-[5-methylsulfonyl-(benzyloxy)-phenyl]-cyclopent-1-enyl}-benzoic acid benzyl ester (30 mg, 0.059 mmol) in ethanol (5 ml) and 2M sodium hydroxide (1 ml) was left at room temperature for 20 hours then diluted with water, washed with ether and the aqueous phase separated, acidified with 2M hydrochloric acid and extracted with ether. The organic extract was dried (MgSO4), evaporated to dryness and the residue triturated with iso-hexane to yield the title compound as a white solid. (14 mg, 57%).

Workup

  1. washwashed with ether
  2. customthe aqueous phase separated
  3. extractionextracted with ether
  4. extractionThe organic extract
  5. dry with materialwas dried (MgSO4)
  6. customevaporated to dryness
  7. customthe residue triturated with iso-hexane

Sources & evidence

ORD record
ord-407b945b8060440197b9b517eaf22bc0
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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