Sodium Hydroxide → HCID 67148752, compound

HRID 2428106Notes

Reaction equation

HRID 2428106 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8](=[O:30])[N:9]([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)[CH:10]1[CH2:12][CH2:11]1)([CH3:6])([CH3:5])[CH3:4]>CO>[C:3]([O:7][C:8](=[O:30])[N:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([CH2:21][OH:22])[CH:15]=1)[CH:10]1[CH2:12][CH2:11]1)([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131728340HCID 131728340, compound

Product 1

HCID 67148752HCID 67148752, compoundYield 107.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aq. 1M NaOH (16 mL) was added to a sol. of [3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzyl]-cyclopropyl-carbamic acid tert-butyl ester (700 mg, 1.64 mmol) in MeOH (32 mL). The mixture was heated to reflux for 2 h, and was allowed to cool to rt. The solvents were partially removed under reduced pressure, and the resulting aq. layer was diluted with water (100 mL). The mixture was extracted with Et2O (3×). The combined org. layers were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 40:60) yielded the title compound (550 mg, quantitative yield). LC-MS: tR=0.98 min; ES+: 312.04.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. customThe solvents were partially removed under reduced pressure
  4. additionthe resulting aq. layer was diluted with water (100 mL)
  5. extractionThe mixture was extracted with Et2O (3×)
  6. dry with materiallayers were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure
  9. customPurification of the crude by FC (EtOAc/heptane 40:60)

Sources & evidence

ORD record
ord-0b2c8d46e0de43c2aa6e7cc4540265ae
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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