Hydrochloric Acid → 6-Fluoro-5-(methanesulfonyl-methylamino)-N-methyl-N-propyl-isophthalamic acid

HRID 1436723Notes

Reaction equation

HRID 1436723 reaction equation
C([O:3][C:4](=[O:25])[C:5]1[C:17]([F:18])=[C:16]([N:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH3:20])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)C.[OH-].[Na+].Cl>C1COCC1>[F:18][C:17]1[C:5]([C:4]([OH:25])=[O:3])=[CH:6][C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])=[CH:15][C:16]=1[N:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 688171926-Fluoro-5-(methanesulfonyl-methylamino)-N-methyl-N-propyl-isophthalamic acid ethyl ester

Product 1

HCID 688175816-Fluoro-5-(methanesulfonyl-methylamino)-N-methyl-N-propyl-isophthalamic acidYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve the 6-fluoro-5-(methanesulfonyl-methyl-amino)-N-methyl-N-propyl-isophthalamic acid ethyl ester (110 mg, 0.30 mmol) in THF (7.5 mL). Add 1 N sodium hydroxide solution (1.48 mL, 1.48 mmol) and stir the resulting biphasic mixture vigorously for 4 h. Acidify with 1 N HCl (1.55 mL, 1.55 mmol) and concentrate the solution to a volume of about 3 mL. Extract the solution with diethyl ether (2×20 mL). Combine the organic layers, dry (magnesium sulfate) and concentrate to give the title compound as a solid (95.2 mg, 93%).

Workup

  1. concentrationconcentrate the solution to a volume of about 3 mL
  2. extractionExtract the solution with diethyl ether (2×20 mL)
  3. dry with materialCombine the organic layers, dry (magnesium sulfate)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-5443725e688147beaae1cea208c3403b
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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