Hydrochloric Acid → 1-(3-Phenylacryloyl)-L-proline

HRID 1590806Notes

Reaction equation

HRID 1590806 reaction equation
[OH-].[Na+].CO.C[O:6][C:7](=[O:23])[C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:22])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>O>[C:13]([N:9]1[CH2:10][CH2:11][CH2:12][C@H:8]1[C:7]([OH:23])=[O:6])(=[O:22])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 53772128HCID 53772128, compound

Product 1

HCID 544467801-(3-Phenylacryloyl)-L-prolineYield 88.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5N sodium hydroxide (18.58 ml) was added dropwise to a methanol solution (100 ml) of N-cinnamoyl-L-proline methyl ester (20.07 g) under ice cooling, and the mixture was stirred at room temperature for three hours. The pH value of the obtained reaction solution was adjusted to 5 with 5N hydrochloric acid, and the resultant solution was poured into 1 l of water. The precipitate was filtered out and dried to obtain 16.84 g of N-cinnamoyl-L-proline.

Workup

  1. customThe pH value of the obtained reaction solution
  2. filtrationThe precipitate was filtered out
  3. customdried

Sources & evidence

ORD record
ord-fe2d97b6b57649c68bfbf9e46cdd4e50
Source dataset
uspto-grants-1993_04
Patent number
US05204462

Reaction notes

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