Maleic Acid → HCID 70403916, compound

HRID 4368Notes

Reaction equation

HRID 4368 reaction equation
[C:1]([O:5][C:6](=[O:17])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:16])[C@H:13]([CH3:15])[NH2:14])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([O:20][C:21](=[O:32])/[CH:22]=[CH:23]/[C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:19].[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37]>C1C=CC=CC=1>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37].[C:1]([O:5][C:6](=[O:17])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:16])[C@H:13]([CH3:15])[NH:14][C@H:22]([C:21]([O:20][CH2:18][CH3:19])=[O:32])[CH2:23][C:24]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:31])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 444266Maleic AcidHCID 5369605Ethyl (2E)-4-oxo-4-phenyl-2-butenoateHCID 12939800tert-Butyl L-alanyl-L-prolinate

Product 1

HCID 70403916HCID 70403916, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4.84 g (20 mmoles) of (S)-alanyl-(S)-proline-t-butylester are dissolved in 40 ml of dry benzene and 4.08 g (20 mmoles) of E-ethyl-3-benzoyl-acrylate are added at room temperature under stirring. After one hour stirring at room temperature the solvent is evaporated off under reduced pressure, the residue is dissolved in 20 ml of ethyl acetate and 2.32 g (20 mmoles) of maleinic acid are added. The precipitated crystals are filtered off after one hour standing and washed with 20 ml of ethyl acetate. 6.7 g (60%) of product are obtained with a melting point of 109°-110° C.

Workup

  1. stirringAfter one hour stirring at room temperature the solvent
  2. customis evaporated off under reduced pressure
  3. dissolutionthe residue is dissolved in 20 ml of ethyl acetate
  4. filtrationThe precipitated crystals are filtered off after one hour standing
  5. washwashed with 20 ml of ethyl acetate

Sources & evidence

ORD record
ord-f01be8f761ca4562ae3496ae6ef3ae07
Source dataset
uspto-grants-1988_02
Patent number
US04725617

Reaction notes

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