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

HRID 1397842Notes

Reaction equation

HRID 1397842 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 (16, 1.20 g, 4.3 mmol) in 28 mL of dichloromethane, pyridine (0.52 mL, 6.4 mmol) and propane-1-sulfonyl chloride (4, 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 the filtrate concentrated under vacuum. The desired compound was isolated with silica gel column chromatography to give a colorless oil (17, 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. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-bcfb90764f87439ba8868275711448f8
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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