HCID 13036861, compound → HCID 13036863, compound

HRID 1156743Notes

Reaction equation

HRID 1156743 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@H:11]2[CH2:14][N:13]([O:15]CC3C=CC=CC=3)[C:12]2=[O:23])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd]>[OH:15][N:13]1[CH2:14][C@H:11]([NH:10][C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:12]1=[O:23]

Participants

3

Reactant 1

HCID 13036861HCID 13036861, compound

Product 1

HCID 13036863HCID 13036863, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To an ethanolic (100 ml) solution of (S)-3-[(phenylacetyl)amino]-1-[(phenylmethyl)oxy]-2-azetidinone (0.8 g, contaminated with triphenylphosphine) is added 10% palladium on charcoal catalyst (0.4 g) and the mixture is hydrogenated under ca. 1 atom pressure for one hour. The reaction mixture is filtered through prewashed Celite and concentrated under reduced pressure to an oily residue. The product is partitioned between 50% sodium bicarbonate solution and ethyl acetate. The aqueous layer is acidified with potassium bisulfate and extracted with ethyl acetate (three 50 ml portions). The combined extracts are dried over sodium sulfate and concentrated to a crystalline solid (ca. 200 mg). Recrystallization from methanol/chloroform affords an analytical sample, melting point 145°-146° C. dec.

Workup

  1. filtrationThe reaction mixture is filtered through prewashed Celite
  2. concentrationconcentrated under reduced pressure to an oily residue
  3. customThe product is partitioned between 50% sodium bicarbonate solution and ethyl acetate
  4. extractionextracted with ethyl acetate (three 50 ml portions)
  5. dry with materialThe combined extracts are dried over sodium sulfate
  6. concentrationconcentrated to a crystalline solid (ca. 200 mg)
  7. customRecrystallization from methanol/chloroform
  8. customaffords an analytical sample, melting point 145°-146° C. dec.

Sources & evidence

ORD record
ord-b48b505d1dbf42e381ce4be426b71d35
Source dataset
uspto-grants-1982_06
Patent number
US04337197

Reaction notes

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