Hydrochloric Acid → (-)-cis-Isocitric acid lactone
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]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
16.49 g of 3-tert-butyl 1,2-diethyl (1S,2R)-1-hydroxy-1,2,3-propanetricarboxylate prepared in Reference Example 5(1), 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 the hydrochloric acid were distilled off under reduced pressure, and the residue was dissolved in 100 ml of acetic acid and 50 ml of concentrated hydrochloric acid again and stirred at 70° C. for 12 hours. The acetic acid and the hydrochloric acid were distilled off under reduced pressure, and the residue was mixed with 100 ml of trifluoroacetic acid and stirred at 60° C. for 5 hours. The trifluoroacetic acid was distilled off under reduced pressure, and the residue was crystallized from hexane-ethyl acetate to give 9.38 g of the title compound as a white powder.
Workup
- additionwere mixed
- distillationThe acetic acid and the hydrochloric acid were distilled off under reduced pressure
- dissolutionthe residue was dissolved in 100 ml of acetic acid
- stirring50 ml of concentrated hydrochloric acid again and stirred at 70° C. for 12 hours
- distillationThe acetic acid and the hydrochloric acid were distilled off under reduced pressure
- additionthe residue was mixed with 100 ml of trifluoroacetic acid
- stirringstirred at 60° C. for 5 hours
- distillationThe trifluoroacetic acid was distilled off under reduced pressure
- customthe residue was crystallized from hexane-ethyl acetate
Sources & evidence
- ORD record
- ord-ef284828323848cc977df982d723e67a
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06048894
Reaction notes
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