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

HRID 1098404Notes

Reaction equation

HRID 1098404 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>C(Cl)Cl>[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 (48, 1.20 g, 4.3 mmol) in methylene chloride (28 mL) was added pyridine (0.52 mL, 6.4 mmol) and propanesulfonyl chloride (0.685 g, 4.8 mmol). 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 give a colorless oil (49, 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-b66a7a1ea8604fc18997e6b88ef71045
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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