Sodium Hydroxide → HCID 59550267, compound

HRID 883725Notes

Reaction equation

HRID 883725 reaction equation
C([O:4][C@@H:5]1[C@H:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]C)=[O:17])[C@@H:8]([CH2:20][CH2:21][CH:22]([OH:30])[C:23]([F:29])([F:28])[CH2:24][CH2:25][CH2:26][CH3:27])[C@H:7]([O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[CH2:6]1)(=O)C.[OH-].[Na+]>C(O)C>[F:29][C:23]([F:28])([CH2:24][CH2:25][CH2:26][CH3:27])[CH:22]([OH:30])[CH2:21][CH2:20][C@H:8]1[C@H:7]([O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[CH2:6][C@H:5]([OH:4])[C@@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59644966HCID 59644966, compound

Product 1

HCID 59550267HCID 59550267, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 7-[(1R,2R,3R,5S)-5-acetoxy-2-(4,4-difluoro-3-hydroxyoctyl)-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanate (16) (70.62 g, 132.1 mmol) in ethanol (213 ml) was cooled on ice, and an 8N-sodium hydroxide aqueous solution (132 ml, 1056 mmol) was added thereto drop wise. After stirring at room temperature for approximately hours, the reaction mixture was concentrated under reduced pressure. The residue was supplemented with water (280 ml) and t-butyl methyl ether (141 ml), and cooled on ice. After 6N-hydrochloric acid was added drop wise to adjust to pH 3 to 4, the solution was extracted three times with ethyl acetate (280 ml). The organic layers were combined and sequentially washed with water (280 ml) twice and saturated aqueous sodium chloride (336 ml). After drying with anhydrous magnesium sulfate (50 g), the solution was concentrated under reduced pressure to give crude 7-[(1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanoic acid (17) as white solid. The entire amount was used in the following step without purification.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. temperaturecooled on ice
  3. additionAfter 6N-hydrochloric acid was added drop wise
  4. extractionthe solution was extracted three times with ethyl acetate (280 ml)
  5. washsequentially washed with water (280 ml) twice
  6. dry with materialAfter drying with anhydrous magnesium sulfate (50 g)
  7. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f01719b1dbb042c28e5c203b35db9059
Source dataset
uspto-grants-2012_08
Patent number
US08236969B2

Reaction notes

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