Hydrochloric Acid → N-[beta-(2-furyl)acryloyl]glutamic acid

HRID 64929Notes

Reaction equation

HRID 64929 reaction equation
O.[OH-].[Na+].[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH:9]=[CH:10][C:11]([NH:13][C@H:14]([C:20]([O-:22])=[O:21])[CH2:15][CH2:16][C:17]([O-:19])=[O:18])=[O:12].Cl>CO>[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH:9]=[CH:10][C:11]([NH:13][C@H:14]([C:20]([OH:22])=[O:21])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 86740992N-[beta-(2-furyl)acryloyl]glutamate

Product 1

HCID 54218369N-[beta-(2-furyl)acryloyl]glutamic acidYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 400 ml of water, 80 ml of methanol and 45 g of sodium hydroxide was added 100 g of the dimethyl DL-N-[β-(2-furyl)acryloyl]glutamate, and the resulting mixture was heated at 60° C. to 65° C. for 4 hours to hydrolyze the ester. The reaction mixture was cooled to room temperature and acidified with hydrochloric acid, and thereafter the precipitated crystals were collected by filtration to obtain 80 g (yield 90%) of DL-N-[β-(2-furyl)acryloyl]glutamic acid having a melting point of 166°-170° C.

Workup

  1. temperaturethe resulting mixture was heated at 60° C. to 65° C. for 4 hours
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-d4cddf9852624eff9a7159c440f27385
Source dataset
uspto-grants-1986_09
Patent number
US04610983

Reaction notes

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