Methanol → HCID 11397324, compound

HRID 1835038Notes

Reaction equation

HRID 1835038 reaction equation
C([O:4][CH:5]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[C:25]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:24]=1)[C:6]([C@H:11]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[CH:12]1[CH2:14][CH2:13]1)([F:10])[C:7]([O-:9])=[O:8])(=O)C.[OH-].[Na+].CO>O1CCCC1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C@H:11]([CH:12]2[CH2:14][CH2:13]2)[C:6]([F:10])([CH:5]([OH:4])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:24]=2)[C:7]([OH:9])=[O:8])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86584691HCID 86584691, compound

Product 1

HCID 11397324HCID 11397324, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl (2R,3S or 2S,3R)-3-(acetyloxy)-2-[(S)-(4-chlorophenyl)(cyclopropyl)methyl]-2-fluoro-4-(4-fluoro-3-phenoxyphenyl)butanoate (Diastereomer B) (0.80 g, 1.50 mmol), aqueous sodium hydroxide (25 ml), methanol (20 ml) and tetrahydrofuran (5 ml) is refluxed for 1 hour. The organic solvents are removed in vacuo, the mixture is diluted with ethyl acetate and acidified to pH 3 with concentrated hydrochloric acid. The organic layer is separated, dried over anhydrous sodium sulfate and concentrated in vacuo to afford the title compound as a colorless semi solid, which is characterized by 1HNMR and 19FNMR and used without further purification.

Workup

  1. temperatureis refluxed for 1 hour
  2. customThe organic solvents are removed in vacuo
  3. additionthe mixture is diluted with ethyl acetate
  4. customThe organic layer is separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-37b44d4078534d95afbd0bef1d8ecc2b
Source dataset
uspto-grants-2004_08
Patent number
US06770463B2

Reaction notes

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