2,3-Dihydroxybutanedioic Acid → HCID 86749736, compound

HRID 1078413Notes

Reaction equation

HRID 1078413 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[C:11]([OH:20])(=[O:19])[CH:12]([CH:14]([C:16]([OH:18])=[O:17])[OH:15])[OH:13]>>[C:16]([CH:14]([CH:12]([C:11]([OH:20])=[O:19])[OH:13])[OH:15])([OH:18])=[O:17].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 978031-(4-Chlorophenyl)ethylamine

Product 1

HCID 86749736HCID 86749736, compound

Procedure

The (+)-enantiomer (starting material for Example 56) was prepared in conventional manner as follows. A mixture of (±)1-(4-chlorophenyl)ethylamine (73 g) and D(-) tartaric acid (70 g) in industrial methylated spirits (IMS) (4.2 1) was allowed to stand at ambient temperature for 2 days. The solid formed was collected by filtration, washed with IMS and recrystallised from IMS to give (+)1-(4-chlorophenyl)ethylamine (-) tartrate, m.p. 195°-199° C. The salt was suspended in water and basified with aqueous ammonia (specific gravity 0.88). The mixture was extracted with diethyl ether to give (+)1-(4-chlorophenyl)ethylamine which was distilled at 120°-125° C. (30 mmHg). Chiral HPLC indicated enantiomeric purity of 97.4%.

Workup

  1. customThe (+)-enantiomer (starting material for Example 56) was prepared in conventional manner
  2. customThe solid formed
  3. filtrationwas collected by filtration
  4. washwashed with IMS
  5. customrecrystallised from IMS

Sources & evidence

ORD record
ord-1be301723dba4d59bbe12ed5c34801c1
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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