Benzyl chloroformate → 3-{[(Benzyloxy)carbonyl]amino}-4-fluorobenzoic acid

HRID 925088Notes

Reaction equation

HRID 925088 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>O1CCCC1.O>[CH2:22]([O:21][C:19]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=[O:6])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 10796Cesium carbonateHCID 753963-Amino-4-fluorobenzoic acid

Product 1

HCID 608273383-{[(Benzyloxy)carbonyl]amino}-4-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-amino-4-fluorobenzoic acid (30 g, 193 mmol) in a mixture of tetrahydrofuran (300 mL) and water (300 mL) was added cesium carbonate (157 g, 483 mmol) and benzyl chloroformate (30.4 mL, 213 mmol). This mixture was stirred at ambient temperature for 16 hours, and was concentrated to about 200 mL. The residue was acidified with 2N HCl to a pH 3, and was partitioned between ethyl acetate and brine. The precipitated solid was collected by filtration, washed with ethyl acetate and water, and dried to provide the title compound. MS (DCI/NH3) m/z 290 (M+H)+.

Workup

  1. concentrationwas concentrated to about 200 mL
  2. customwas partitioned between ethyl acetate and brine
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with ethyl acetate and water
  5. customdried

Sources & evidence

ORD record
ord-45052d68242b43a493bc5049378a47c7
Source dataset
uspto-grants-2016_03
Patent number
US09283222B2

Reaction notes

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