Sodium Hydroxide → HCID 67148487, compound

HRID 2428117Notes

Reaction equation

HRID 2428117 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8](=[O:31])[N:9]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:22](C)(C)[O:23][SiH2]C(C)(C)C)[CH:16]=1)[CH:10]1[CH2:12][CH2:11]1)([CH3:6])([CH3:5])[CH3:4]>CO>[C:3]([O:7][C:8](=[O:31])[N:9]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([CH2:22][OH:23])[CH:16]=1)[CH:10]1[CH2:11][CH2:12]1)([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131728341HCID 131728341, compound

Product 1

HCID 67148487HCID 67148487, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aq. 1M NaOH (48 mL) was added to a suspension of {2-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-phenyl]-ethyl}-cyclopropyl-carbamic acid tert-butyl ester (2.10 g, 4.77 mmol) in MeOH (96 mL). The mixture was heated to reflux for 90 min. The mixture was allowed to cool to rt, and the solvents were partially removed under reduced pressure. The resulting aq. mixture was diluted with water (100 mL), and was extracted with Et2O (3×). The combined org. extracts 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 (1.34 g, 86%). LC-MS: tR=0.98 min; ES+: 326.30.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 90 min
  3. customthe solvents were partially removed under reduced pressure
  4. additionThe resulting aq. mixture was diluted with water (100 mL)
  5. extractionwas extracted with Et2O (3×)
  6. dry with materialextracts 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-faca85e1f7034814b4d97a9799ea8b75
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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