Methanol → 2-Fluoro-3-(propane-1-sulfonylamino)-benzoic acid methyl ester

HRID 1397845Notes

Reaction equation

HRID 1397845 reaction equation
[F:1][C:2]1[C:10]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:18]N(C)C=O.C(Cl)(=O)C(Cl)=O.CO>ClCCl>[CH3:18][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])[C:2]=1[F:1]

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 580865772-Fluoro-3-(propylsulfonamido)benzoic acid

Product 1

HCID 579632422-Fluoro-3-(propane-1-sulfonylamino)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 2-fluoro-3-(propane-1-sulfonylamino)-benzoic acid (19, 5.05 g, 19.3 mmol) in 100 mL of dichloromethane, N,N-dimethylformamide (0.075 mL, 0.97 mmol) was added under an atmosphere of nitrogen. The reaction was cooled with ice/water, followed by slow addition of oxalyl chloride (2.00 M in dichloromethane, 10.8 mL, 21.6 mmol). The reaction mixture was stirred at room temperature for 3.0 hours. The reaction was cooled with ice/water, followed by addition of methanol (36.0 mL, 0.89 mol) slowly. The reaction was stirred at room temperature overnight. The reaction was concentrated under vacuum and purified with silica gel column chromatography eluting with 30% ethyl acetate in hexane to give the desired compound as a crude white solid (20, 4.0 g), used in the next step without further purification.

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. concentrationThe reaction was concentrated under vacuum
  3. custompurified with silica gel column chromatography
  4. washeluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9fd3b668c7794fd9aed9cd14f321816f
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

Loading…