Potassium Hydroxide → (2R,3S)-2-benzyl-3-hydroxysuccinic acid

HRID 888215Notes

Reaction equation

HRID 888215 reaction equation
[CH2:1]([C@@H:8]([C@@H:15]([OH:22])[C:16]([O:18]C(C)C)=[O:17])[C:9]([O:11]C(C)C)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C1COCC1.O>[CH2:1]([C@H:8]([C@H:15]([OH:22])[C:16]([OH:18])=[O:17])[C:9]([OH:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 10957810HCID 10957810, compound

Product 1

HCID 54300227(2R,3S)-2-benzyl-3-hydroxysuccinic acidYield 29.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Diisopropyl (2S,3R)-2-benzyl-3-hydroxysuccinate (9.76 g; 31.65 mmol; 1.00 eq.) was taken in THF (150 mL), cooled to 0° C. and was treated with KOH (10.65 g; 189.90 mmol; 6.00 eq.) in water (50 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 chilled to 0° C. and cautiously acidified with an aqueous solution of HCl (1 N) until pH 3.8. The solid that separated was collected by filtration to give the title product (single diastereoisomer) as white solid (2.08 g, 29%).

Workup

  1. customTHF was removed
  2. washThe aqueous layer was washed with ether (100 mL)
  3. temperaturewas chilled to 0° C.
  4. customThe solid that separated
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-45c8c73a7c514efca9164b153819d7e8
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

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