(S)-1,1-dibenzyl 2-ethyl propane-1,1,2-tricarboxylate → (S)-2-(1-ethoxy-1-oxopropan-2-yl)malonic acid

HRID 1487174Notes

Reaction equation

HRID 1487174 reaction equation
[CH:1]([C:19]([O:21]CC1C=CC=CC=1)=[O:20])([C:9]([O:11]CC1C=CC=CC=1)=[O:10])[C@@H:2]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:3]>CO.[Pd]>[CH2:7]([O:6][C:4](=[O:5])[C@H:2]([CH:1]([C:19]([OH:21])=[O:20])[C:9]([OH:11])=[O:10])[CH3:3])[CH3:8]

Participants

4

Reactant 1

HCID 86699671(S)-1,1-dibenzyl 2-ethyl propane-1,1,2-tricarboxylate

Product 1

HCID 86699672(S)-2-(1-ethoxy-1-oxopropan-2-yl)malonic acidYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the solution of (S)-1,1-dibenzyl 2-ethyl propane-1,1,2-tricarboxylate (23 g, 0.06 mol) in methanol (500 mL) was added palladium on carbon (10%, 2 g), and then the mixture was stirred under an atmosphere of hydrogen at room temperature overnight. The catalyst was filtrated and the filtrate was concentrated under reduced pressure to afford the crude product (S)-2-(1-ethoxy-1-oxopropan-2-yl)malonic acid, which was purified by silica gel chromatography (10 g, yield 83%).

Workup

  1. filtrationThe catalyst was filtrated
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f00957924cca487ab4b4d6a261d6ac4a
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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