Hydrochloric Acid → HCID 17882379, compound

HRID 369411Notes

Reaction equation

HRID 369411 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:8]=[CH:9][C:10]=1[CH2:11][C:12]1[N:13]([CH3:27])[C:14]([C:18](=[O:26])[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[C:15]([CH3:17])[CH:16]=1)=[O:4].[OH-].[Na+].Cl>CO.C1COCC1.O>[C:3]([C:5]1[CH:6]=[C:7]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:8]=[CH:9][C:10]=1[CH2:11][C:12]1[N:13]([CH3:27])[C:14]([C:18](=[O:26])[C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)=[C:15]([CH3:17])[CH:16]=1)([OH:4])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 17882392HCID 17882392, compound

Product 1

HCID 17882379HCID 17882379, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

N-{3-Methoxycarbonyl-4-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]phenyl}methanesulfonamide (735 mg, 1.54 mmol) and 2.5 N sodium hydroxide (2.5 ml) were dissolved in a 1:1 mixture of methanol-THF (40 ml) and stirred at room temperature for 64 h. The mixture was diluted with water, acidified to pH 2 with 2.0 N HCl, and extracted with ethyl acetate. The organic extracts were washed with brine, dried over sodium sulfate and concentrated to dryness. Crystallization from methylene chloride-methanol gave N-{3-carboxy-4-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]phenyl}-methanesulfonamide (500 mg, 70%) as a solid, mp 248-250° C. (dec.).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customCrystallization from methylene chloride-methanol

Sources & evidence

ORD record
ord-ec4fdb6b4814444fa9ba66fa09fc38fd
Source dataset
uspto-grants-2000_10
Patent number
US06136844

Reaction notes

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