Sodium Hydroxide → HCID 86632366, compound

HRID 2428146Notes

Reaction equation

HRID 2428146 reaction equation
[C:1]([O:5][C:6](=[O:30])[N:7]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([C:21](C)(C)[O:22][SiH2]C(C)(C)C)[CH:15]=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:30])[N:7]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([CH2:21][OH:22])[CH:15]=1)[CH2:8][CH:9]([F:11])[F:10])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131728964HCID 131728964, compound

Product 1

HCID 86632366HCID 86632366, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

{2-[3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-phenyl]-ethyl}-(2,2-difluoro-ethyl)-carbamic acid tert-butyl ester (7.50 g, 16.2 mmol) was dissolved in MeOH (323 mL). Aq. 1M NaOH (161 mL) was added, and the mixture was heated to reflux for 1 h. The solvents were partially removed under reduced pressure, and the aq. residue was diluted with water (900 mL). The mixture was extracted with Et2O (3×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to yield to crude title compound (4.60 g, 81%) that was used further without purification. LC-MS: tR=1.00 min; ES+: 317.31.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 h
  3. customThe solvents were partially removed under reduced pressure
  4. additionthe aq. residue was diluted with water (900 mL)
  5. extractionThe mixture was extracted with Et2O (3×)
  6. dry with materialextracts were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-25876a17fdc740dd9923de80ff59e2ed
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

Loading…