L-Tartaric acid → 2,3-Dihydroxybutanedioic Acid

HRID 2399181Notes

Reaction equation

HRID 2399181 reaction equation
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3]>CC(C)=O>[C:1]([OH:10])(=[O:9])[CH:2]([CH:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3]

Participants

3

Reactant 1

HCID 444305L-Tartaric acid

Product 1

HCID 8752,3-Dihydroxybutanedioic Acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The free base was dissolved in acetone and treated with one mole equivalent of L-tartaric acid. This mixture was concentrated and treated with dry ether to give a tartaric acid salt of the title compound as a white solid; mp 160°-163° C.; IR (KBr) 3448, 3064, 3030, 1726, 1664, 1612, 1582, 1518 cm-1 ; MS (FAB) MH+ m/z 1070, (M+Na)+ m/z 1092, (M+K)+ m/z 1108; 1H-NMR (CDCl3) δ 1.085 (s, 3H), 1.156 (s, 3H), 1.586 (s, 3H), 1.683 (m, H), 1.894 (s, 3H), 2.063 (m, H), 2.153 (s, 3H), 2.226 (s, 3H), 2.366 (s, 3H), 2.438 (m, 8H), 3.498 (s, 2H), 3.835 (d, H), 4.132 (d, H), 4.254 (d, H), 4.384 (m, H), 4.911 (m, H), 5.617 (m, 2H), 5.974 (m, H), 6.190 (t, H), 6.225 (S, H), 6.967 (d, NH), 7.200-8.200 (m, 19H).

Workup

  1. concentrationThis mixture was concentrated
  2. additiontreated with dry ether

Sources & evidence

ORD record
ord-6cdcfa84cab04a59951c04af3ac9a370
Source dataset
uspto-grants-1995_09
Patent number
USH0001487

Reaction notes

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