Sodium Methoxide → HCID 57749385, compound

HRID 1874364Notes

Reaction equation

HRID 1874364 reaction equation
C(=O)(OC(C)(C)C)[O:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:4]=1.C[O-].[Na+]>CO>[F:9][C:6]1[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][C:5]=1[NH:10][C:11](=[O:12])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 57749294HCID 57749294, compound

Product 1

HCID 57749385HCID 57749385, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3-[(tert-butoxycarbonyl)amino]-4-fluorophenyl tert-butyl carbonate (33.1 g, 101 mmol), sodium methoxide (6.55 g, 121 mmol) and methanol (500 mL) was stirred at 40° C. for 15 hr. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and water were added to the residue. The organic layer was separated, washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was dried to give the title compound (22.8 g, quant.) as a yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate and water
  2. additionwere added to the residue
  3. customThe organic layer was separated
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was dried

Sources & evidence

ORD record
ord-cf2dacc1405241a0bb8b39f087e67222
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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