2,3-Dihydroxybutanedioic Acid → Diisopropylether ethyl acetate

HRID 614652Notes

Reaction equation

HRID 614652 reaction equation
[C:1]([CH:4]([CH:6]([C:8]([O-:10])=[O:9])O)O)([O-])=O.[K+].[K+].[C:13](O)(=O)[CH:14]([CH:16]([C:18](O)=O)[OH:17])O>CC(C)=O>[C:8]([O:10][CH2:13][CH3:14])(=[O:9])[CH3:6].[CH:16]([O:17][CH:4]([CH3:6])[CH3:1])([CH3:18])[CH3:14]

Participants

4

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 6100505Dipotassium 2,3-dihydroxybutanedioate

Product 1

HCID 22281796Diisopropylether ethyl acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6.1 g of crude N-(N-carbobenzoxy-DL-α-hydroxyalanyl)-L-phenylalanyl-L-proline p-nitrophenyl ester obtained in step hi), hii) or hiii) below, in 300 ml acetone, is treated with a 10% (w/v) potassium tartrate solution (having pH = 7.9). The reaction mixture is stirred for 18 hours at room temperature, and worked up by the addition of 10% (w/v) tartaric acid solution until the reaction mixture is at a pH of 5 and extraction with methylene chloride. The product obtained on concentration is crystallized from ethyl acetate or an ethyl acetate/diisopropyl ether mixture (3:1; v/v) yielding, after drying at 90° in a high vacuum, the aci-form of the title compound (M.Pt. 206°-208°; decomposition); [α]D20 = -28° (c = 0.5 in CH3OH).

Workup

  1. extractionis at a pH of 5 and extraction with methylene chloride
  2. customThe product obtained on concentration
  3. customis crystallized from ethyl acetate

Sources & evidence

ORD record
ord-ee0df50b7d11439e8ffa294edc05eaab
Source dataset
uspto-grants-1979_03
Patent number
US04145549

Reaction notes

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