Acetic Acid → HCID 86738817, compound

HRID 354775Notes

Reaction equation

HRID 354775 reaction equation
[F:1][C:2]1[CH:35]=[CH:34][CH:33]=[CH:32][C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[NH:15][C:16]([C:18]([NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:20])[CH3:19])=[O:17])=[O:5].[C:36]([O-])(C)(C)C.[K+].CI.C(O)(=O)C>C(O)(C)(C)C>[F:1][C:2]1[CH:35]=[CH:34][CH:33]=[CH:32][C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[N:15]([CH3:36])[C:16]([C:18]([NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:19])[CH3:20])=[O:17])=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 54387463HCID 54387463, compound

Product 1

HCID 86738817HCID 86738817, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 500 mg of benzyl [1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]-carbamoyl]-1-methyl-ethyl]carbamate (1.043 mol) and 150 mg of potassium t-butanolate in 20 ml of t-butanol is treated with 0.15 ml of methyl iodide and stirred at room temperature for 2.5 days. The reaction mixture is buffered with glacial acetic acid and concentrated. The residue is partitioned between methylene chloride and 10 percent aqueous sodium bicarbonate solution. After drying the organic phase overnight and concentrating, the residue is chromatographed on a pressure column containing 10 g of silica gel (particle size 0.04-0.06 mm) under 0.2-0.4 atmospheres of nitrogen with methylene chloride/ethyl acetate (20:1) as the elution agent. There is obtained benzyl [1-[[2-(o-fluorobenzoyl)-4-nitrophenyl]-methylcarbamoyl]-1-methyl-ethyl]carbamate of melting point 168°-169° (ether/n-hexane).

Workup

  1. concentrationconcentrated
  2. customThe residue is partitioned between methylene chloride and 10 percent aqueous sodium bicarbonate solution
  3. customAfter drying the organic phase overnight
  4. concentrationconcentrating
  5. customthe residue is chromatographed on a pressure column
  6. additioncontaining 10 g of silica gel (particle size 0.04-0.06 mm) under 0.2-0.4 atmospheres of nitrogen with methylene chloride/ethyl acetate (20:1) as the elution agent

Sources & evidence

ORD record
ord-5bd29afbb2c34d7bbdecb7cc5192ee0c
Source dataset
uspto-grants-1983_03
Patent number
US04377522

Reaction notes

Loading…