N-methyl-2-pyrrolidone → HCID 21997035, compound

HRID 1978219Notes

Reaction equation

HRID 1978219 reaction equation
CN1CCCC1=O.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH2:18][CH:19]([CH2:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C:20]([OH:22])=O)(=[O:17])=[O:16])=[CH:11][CH:10]=1.Cl.CN(C)CCCN=C=NCC.Cl.[NH2:47][OH:48]>C(OCC)(=O)C>[OH:48][NH:47][C:20](=[O:22])[CH:19]([CH2:18][S:15]([C:12]1[CH:11]=[CH:10][C:9]([CH3:8])=[CH:14][CH:13]=1)(=[O:17])=[O:16])[CH2:23][S:24]([C:27]1[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=1)(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 443297Hydroxyamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21997029HCID 21997029, compound

Product 1

HCID 21997035HCID 21997035, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To N-methylpyrrolidinone (20 mL) cooled in an ice bath, is added 2-[(4-methylbenzenesulfonyl)methyl]-3-(4-methylbenzenesulfonyl)-propionoic acid (4.4 g, 11 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.2 g, 22 mmol), and hydroxylamine hydrochloride (1.5 g, 22 mmol). After stirring overnight at ambient temperature, the mixture is transferred to ethyl acetate and extracted with aqueous 10% hydrochloric acid, distilled water, aqueous sodium bicarbonate, brine, and dried over anhydrous sodium sulfate. The organic phase is concentrated in vacuo and triturated from hexane to afford the title compound as a white solid.

Workup

  1. extractionextracted with aqueous 10% hydrochloric acid
  2. distillationdistilled water, aqueous sodium bicarbonate, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe organic phase is concentrated in vacuo
  5. customtriturated from hexane

Sources & evidence

ORD record
ord-0919ae49d8fd45de890226c347a29578
Source dataset
uspto-grants-2001_05
Patent number
US06235928B1

Reaction notes

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