Sodium Hydroxide → HCID 67148759, compound

HRID 2428139Notes

Reaction equation

HRID 2428139 reaction equation
[CH3:1][O:2][C:3](=[O:22])[NH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([C:13](C)(C)[O:14][SiH2]C(C)(C)C)[CH:7]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:22])[NH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([CH2:13][OH:14])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131728963HCID 131728963, compound

Product 1

HCID 67148759HCID 67148759, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of [3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzyl]-carbamic acid methyl ester (5.39 g, 15.7 mmol) in MeOH (160 mL) and aq. 1M NaOH (80 mL) was heated to 80° C. for 1.5 h. The mixture was allowed to cool to rt, and was partially evaporated under reduced pressure. The aq. residue was extracted with EtOAc (3×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (3.53 g, 98%) that was used further without purification. LC-MS: tR=0.72 min; ES+: 230.25.

Workup

  1. temperatureto cool to rt
  2. customwas partially evaporated under reduced pressure
  3. extractionThe aq. residue was extracted with EtOAc (3×)
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customDrying the residue under high vacuum

Sources & evidence

ORD record
ord-64cf38d61fe34508aa08f72eba138bf1
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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