Water → HCID 54293706, compound

HRID 846226Notes

Reaction equation

HRID 846226 reaction equation
[C:1]([C:4]1[CH:32]=[CH:31][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28]C)=[O:27])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[C:6]([CH2:33][CH2:34][CH3:35])[C:5]=1[OH:36])(=[O:3])[CH3:2].[OH-].[Na+].O>C1COCC1>[C:1]([C:4]1[CH:32]=[CH:31][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[C:6]([CH2:33][CH2:34][CH3:35])[C:5]=1[OH:36])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 19884813HCID 19884813, compound

Product 1

HCID 54293706HCID 54293706, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Step C above, (800 mg, 1.54 mmoles, 1N NaOH (3.2 ml), water (3.2 ml) and THF (10 ml) were stirred at room temperature for three hours. The THF layer was removed and the aqueous portion diluted with water and extracted with ether. The aqueous portion was acidified with concentrated HCl. A solid precipitate formed which was extracted into ether, dried and concentrated. Trituration of the residue with ether-methanol afforded the title compound; mp 138°-140°.

Workup

  1. customThe THF layer was removed
  2. additionthe aqueous portion diluted with water
  3. extractionextracted with ether
  4. customA solid precipitate formed which
  5. extractionwas extracted into ether
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c0d583675d9d4595bdb460d6c170aef3
Source dataset
uspto-grants-1992_08
Patent number
US05135940

Reaction notes

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