ethyl(2S)-3-{4-[2-(benzyloxy)-2-oxoethoxy]phenyl}-2-ethoxypropanoate → {4-[(2S)-2,3-Diethoxy-3-oxopropyl]phenoxy}acetic Acid

HRID 2374638Notes

Reaction equation

HRID 2374638 reaction equation
C([O:8][C:9](=[O:28])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([O:25][CH2:26][CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14][CH:13]=1)C1C=CC=CC=1>[Pd].C1COCC1>[CH2:26]([O:25][C@H:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][C:9]([OH:28])=[O:8])=[CH:13][CH:14]=1)[CH3:27]

Participants

4

Reactant 1

HCID 11383604ethyl(2S)-3-{4-[2-(benzyloxy)-2-oxoethoxy]phenyl}-2-ethoxypropanoate

Product 1

HCID 11162260{4-[(2S)-2,3-Diethoxy-3-oxopropyl]phenoxy}acetic AcidYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl(2S)-3-{4-[2-(benzyloxy)-2-oxoethoxy]phenyl}-2-ethoxypropanoate (22.33 g, 57.8 mmol) in freshly distilled THF (290 mL) was added Pd/C (10%, 3.1 g) and the reaction mixture was hydrogenated under atmospheric pressure at room temperature overnight. The mixture was filtered through a plug of Celite and the filtrate was concentrated in vacuo to afford 16.6 g (97%) of a light yellow oil.

Workup

  1. filtrationThe mixture was filtered through a plug of Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-947f617caadc49b1b34615e8cb68fa05
Source dataset
uspto-grants-2008_12
Patent number
US07462644B2

Reaction notes

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