Potassium Hydroxide → D-Erythro-3-Methylmalate
Reaction equation
[OH:1][C@H:2]([C@H:9]([CH3:16])[C:10]([O:12]C(C)C)=[O:11])[C:3]([O:5]C(C)C)=[O:4].[OH-].[K+]>C1COCC1.O>[OH:1][C@H:2]([C@H:9]([CH3:16])[C:10]([OH:12])=[O:11])[C:3]([OH:5])=[O:4]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Diisopropyl (2R,3S)-2-hydroxy-3-methylsuccinate (9.75 g; 42.0 mmol; 1.00 eq.) was taken in THF (146 mL), cooled to 0° C. and was treated with KOH (14.1 g, 152 mmol) in water (49 mL). The resulting mixture was stirred at RT for 48 h. THF was removed and the residue was taken in water. The aqueous layer was washed with ether (100 mL) and was acidified with an aqueous solution of HCl (1.5 N), then was extracted with EtOAc (continuous extraction during 20 hours). The organic phase was dried over Na2SO4 and then concentrated to give the title product (mixture of diastereoisomers) as a pale yellow oil (2.49 g).
Workup
- customTHF was removed
- washThe aqueous layer was washed with ether (100 mL)
- extractionwas extracted with EtOAc (continuous extraction during 20 hours)
- dry with materialThe organic phase was dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-470c4fdfd8784dbba0aed705d218b182
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247437B2
Reaction notes
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