L-Malic Acid → HCID 131716221, compound

HRID 329420Notes

Reaction equation

HRID 329420 reaction equation
[CH2:1]([C:7]([OH:9])=[O:8])[C@H:2]([OH:6])[C:3]([OH:5])=[O:4].Cl.[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]([NH2:27])[CH2:20]C2C=CC=CC=2)=[CH:15][CH:14]=1)=[CH2:12].C(C1C=CC([C@@H](N)C)=CC=1)=C>CO>[C:3]([OH:5])(=[O:4])[C@H:2]([CH2:1][C:7]([OH:9])=[O:8])[OH:6].[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([C@H:19]([NH2:27])[CH3:20])=[CH:15][CH:14]=1)=[CH2:12]

Participants

5

Reactant 3

HCID 222656L-Malic AcidHCID 51358467HCID 51358467, compoundHCID 67924873HCID 67924873, compound

Product 1

HCID 131716221HCID 131716221, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

37.4 g (0.279 mol) of L-(-)-malic acid are added to a solution of 41.06 g (0.279 mol) of (R), (S)-1-(4-vinylphenyl)-ethylamine in 250 ml of methanol at 0° C. After 15 hours, the precipitated crystals (31.0 g) are filtered off under suction, and the mother liquor is evaporated down in vacuo until crystallization begins again. A further 15 g of product are obtained. The crystal fractions are combined and recrystallized twice, in each case from 250 ml of methanol, with the addition of about 50 mg of di-tert-butyl-p-cresol. Yield: 15.2 g of white crystalline powder, [α]D20 =+2.10° (H2O, c=0.95).

Workup

  1. filtrationthe precipitated crystals (31.0 g) are filtered off under suction
  2. customthe mother liquor is evaporated down in vacuo until crystallization

Sources & evidence

ORD record
ord-23904ba9649f4313bf92b0fc900724c4
Source dataset
uspto-grants-1990_01
Patent number
US04891412

Reaction notes

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