Ethyl Acetate → HCID 71127320, compound

HRID 1912048Notes

Reaction equation

HRID 1912048 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([CH:16]([CH2:25][CH2:26][O:27]CC1C=CC=CC=1)[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C>[OH-].[Pd+2].[OH-].O1CCCC1>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14]([CH:16]([CH2:25][CH2:26][OH:27])[CH2:17][C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 71127319HCID 71127319, compound

Product 1

HCID 71127320HCID 71127320, compoundYield 112.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-5-benzyloxyvalerate (500 g), ethyl acetate (750 mL) and tetrahydrofuran (1510 mL) were mixed. To the mixture was added 20 w/w % palladium hydroxide (50 g). The mixture was stirred for 4.5 hr under hydrogen atmosphere (1 atm). The palladium hydroxide was filtered off and the filtrate was concentrated in vacuo to give the title compound (455.76 g) as a crude product.

Workup

  1. filtrationThe palladium hydroxide was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9d112999d2734f6fa5540c8bf533fb21
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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