Sodium Hydroxide → HCID 86622950, compound

HRID 2428161Notes

Reaction equation

HRID 2428161 reaction equation
[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([C:20](C)(C)[O:21][SiH2]C(C)(C)C)[CH:14]=1)[CH2:8][CH:9]([F:11])[F:10])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([CH2:20][OH:21])[CH:14]=1)[CH2:8][CH:9]([F:11])[F:10])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131728333HCID 131728333, compound

Product 1

HCID 86622950HCID 86622950, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzyl]-(2,2-difluoro-ethyl)-carbamic acid tert-butyl ester (4.35 g, 9.67 mmol) was suspended in MeOH (100 mL), and aq. 1M NaOH (50 mL) was added. The mixture was heated to reflux for 3 h, and the solvents were partially removed under reduced pressure. The aq. residue was diluted with water (100 mL), and the mixture was extracted with EtOAc (3×). The combined org. extracts were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 2:8→3:7) yielded the title compound (2.70 g, 83%). LC-MS: tR=0.99 min; ES+: 302.96.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 h
  3. customthe solvents were partially removed under reduced pressure
  4. additionThe aq. residue was diluted with water (100 mL)
  5. extractionthe mixture was extracted with EtOAc (3×)
  6. washextracts were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvents were removed under reduced pressure
  10. customPurification of the crude by FC (EtOAc/heptane 2:8→3:7)

Sources & evidence

ORD record
ord-a1cbf5234dd640e8b203037efe92a1db
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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