Water → HCID 66975646, compound

HRID 1022645Notes

Reaction equation

HRID 1022645 reaction equation
[CH2:1]([N:8]([CH2:13][CH:14]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=1)[CH:15]([OH:25])[CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].O>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH:14]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[CH:15]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:22])[CH3:23])([CH3:19])[CH3:20])[O:25][CH2:10][C:9]1=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 66975923HCID 66975923, compound

Product 1

HCID 66975646HCID 66975646, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-benzyl-N-[(2RS,3RS)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,4-dichlorophenyl)-3-hydroxybutyl]-2-chloroacetamide (44.7 g) in THF (450 ml) was added sodium methoxide (5.46 g) at 0° C. The mixture was stirred at room temperature for 2 hr, water was added, and methanol was evaporated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (10%-50%)) to give the title compound (40.6 g) as a pale-yellow oil.

Workup

  1. custommethanol was evaporated under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (10%-50%))

Sources & evidence

ORD record
ord-e2675c390b164ab7afd2c47bdd1ea58d
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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