Water → 6-Chloro-2-fluoro-(propane-1-sulfonylamino)-benzoic acid benzyl ester

HRID 1639585Notes

Reaction equation

HRID 1639585 reaction equation
[CH2:1]([O:8][C:9](=[O:19])[C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH2:26]([S:29](Cl)(=[O:31])=[O:30])[CH2:27][CH3:28].O>ClCCl>[CH2:1]([O:8][C:9](=[O:19])[C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[C:12]([NH:17][S:29]([CH2:26][CH2:27][CH3:28])(=[O:31])=[O:30])[C:11]=1[F:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 662791-Propanesulfonyl chlorideHCID 58087305Benzyl 3-amino-6-chloro-2-fluorobenzoate

Product 1

HCID 580867966-Chloro-2-fluoro-(propane-1-sulfonylamino)-benzoic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-amino-6-chloro-2-fluoro-benzoic acid benzyl ester (12, 1.20 g, 4.3 mmol) in 28 mL of dichloromethane, pyridine (0.52 mL, 6.4 mmol) and propanesulfonyl chloride (0.685 g, 4.8 mmol) were added. The reaction was stirred at room temperature overnight, then poured into water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The desired compound was isolated with silica gel column chromatography to provide the desired compound as a colorless oil (13, 960 mg, 58.0%). MS (ESI) [M−H+]−=384.1.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4757f9609c934ce2aeffbd62863f3bde
Source dataset
uspto-grants-2012_02
Patent number
US08110576B2

Reaction notes

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