Water → Benzyl 2,6-difluoro-3-(propane-1-sulfonamido)benzoate

HRID 1397832Notes

Reaction equation

HRID 1397832 reaction equation
[CH2:1]([O:8][C:9](=[O:19])[C:10]1[C:15]([F: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]([F: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 53396458Benzyl 3-amino-2,6-difluorobenzoate

Product 1

HCID 53396460Benzyl 2,6-difluoro-3-(propane-1-sulfonamido)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-amino-2,6-difluoro-benzoic acid benzyl ester (3, 6.00 g, 22.8 mmol) in 150 mL of dichloromethane, pyridine (2.76 mL, 34.2 mmol) and propane-1-sulfonyl chloride (4, 3.80 mL, 33.8 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 the filtrate concentrated under vacuum. The desired compound was isolated with silica gel column chromatography to give a colorless oil (5, 7.0 g, 83.1%). MS(ESI) [M+H+]+=370.1.

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. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-a58e754df71449adaf417d9450a7d1cc
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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