Sodium Hydroxide → HCID 66975364, compound

HRID 1022569Notes

Reaction equation

HRID 1022569 reaction equation
[CH2:1]([N:8]([CH2:13][CH:14]([CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH:15]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([F:24])[CH:18]=1)[OH:16])[C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH:14]([CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH:15]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([F:24])[CH:18]=2)[O:16][CH2:10][C:9]1=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66976073HCID 66976073, compound

Product 1

HCID 66975364HCID 66975364, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-benzyl-N-[(2RS,3SR)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-(4-chloro-3-fluorophenyl)-3-hydroxypropyl]-2-chloroacetamide (34.5 g) in THF (1340 mL) was added 1 N aqueous sodium hydroxide solution (80.0 mL) under ice-cooling, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (31.5 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washThe diluted solution was washed with distilled water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c37ba26d53ad4392a7a512e6f3ff368e
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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