Hydrochloric Acid → (-)-cis-Isocitric acid lactone

HRID 2287496Notes

Reaction equation

HRID 2287496 reaction equation
O[C@H:2]([C:17]([O:19]CC)=[O:18])[C@H:3]([C:12]([O:14]CC)=[O:13])[CH2:4][C:5]([O:7]C(C)(C)C)=[O:6].Cl>C(O)(=O)C>[O:6]=[C:5]1[O:7][C@H:2]([C:17]([OH:19])=[O:18])[C@H:3]([C:12]([OH:14])=[O:13])[CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86751035HCID 86751035, compound

Product 1

HCID 853429(-)-cis-Isocitric acid lactoneYield 99.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

16.49 g of 3-tert-butyl 1,2-diethyl (1S,2R)-1-hydroxy-1,2,3-propanetricarboxylate, 100 ml of acetic acid and 50 ml of concentrated hydrochloric acid were mixed and stirred at 70° C. for 5 hours. The acetic acid and hydrochloric acid were evaporated in vacuo, and the residue was dissolved in 100 ml of acetic acid and 50 ml of concentrated hydrochloric acid again. The resulting solution was stirred at 70° C. for 12 hours. The acetic acid and hydrochloric acid were evaporated in vacuo, and the residue was stirred in 100 ml of trifluoroacetic acid at 60° C. for 5 hours. The trifluoroacetic acid was evaporated in vacuo, and the residue was crystallized in hexane-ethyl acetate to give 9.38 g of the title compound as a white powder.

Workup

  1. customThe acetic acid and hydrochloric acid were evaporated in vacuo
  2. dissolutionthe residue was dissolved in 100 ml of acetic acid
  3. stirringThe resulting solution was stirred at 70° C. for 12 hours
  4. customThe acetic acid and hydrochloric acid were evaporated in vacuo
  5. stirringthe residue was stirred in 100 ml of trifluoroacetic acid at 60° C. for 5 hours
  6. customThe trifluoroacetic acid was evaporated in vacuo
  7. customthe residue was crystallized in hexane-ethyl acetate

Sources & evidence

ORD record
ord-76630c3d7f1d462abbc9910601af08f8
Source dataset
uspto-grants-2000_07
Patent number
US06083985

Reaction notes

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