Ethyl Acetate → HCID 13316706, compound

HRID 1154965Notes

Reaction equation

HRID 1154965 reaction equation
C(OC([N:11]1[C:15](=[O:16])[CH2:14][C@@H:13]([C@H:17]([N:21]2[C:25](=[O:26])[C:24]3=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:31])[C:18]([OH:20])=[O:19])[O:12]1)=O)C1C=CC=CC=1.C(OCC)(=O)C>[Pd].C(O)C>[O:16]=[C:15]1[CH2:14][CH:13]([CH:17]([N:21]2[C:22](=[O:31])[C:23]3=[CH:30][CH:29]=[CH:28][CH:27]=[C:24]3[C:25]2=[O:26])[C:18]([OH:20])=[O:19])[O:12][NH:11]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 12943973HCID 12943973, compound

Product 1

HCID 13316706HCID 13316706, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 7.48 g. (17.6 mM) quantity of (αS,5S) 2-[(benzyloxy)carbonyl]-3-oxo-α-phthalimido-5-isoxazolidine acetic acid is dissolved in 150 ml. of ethyl acetate and 75 ml. of 95% ethanol. The solution is treated with 1.5 g. of palladium black and hydrogenated at 25° C. and 1 atmosphere of pressure. The reaction is stopped after 165 minutes, filtered, and the filtrate is evaporated in vacuo to yield 3-oxo-α-phthalimido-5-isoxazolidine acetic acid as a residue.

Workup

  1. additionThe solution is treated with 1.5 g
  2. customhydrogenated at 25° C.
  3. filtrationfiltered
  4. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-6235436ab8364aa682a5fc738719680d
Source dataset
uspto-grants-1981_11
Patent number
US04298744

Reaction notes

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