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

HRID 1639588Notes

Reaction equation

HRID 1639588 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 (15, 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 (10.8 mL, 2.00 M in dichloromethane, 21.6 mmol). The reaction mixture was stirred at room temperature for 3.0 hours, then cooled with ice water, followed by slowly adding 36.0 mL of methanol. 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. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a crude white solid (16, 4.0 g).

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
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-33ef61f0f5fe4e80a67944d4c2884b1b
Source dataset
uspto-grants-2012_02
Patent number
US08110576B2

Reaction notes

Loading…