HCID 70093171, compound → HCID 70096544, compound

HRID 1603247Notes

Reaction equation

HRID 1603247 reaction equation
C(O[C:9]([NH:11][C@H:12]([C:20]([C@@H:22]1[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[N:24]([NH2:30])[C:23]1=[O:31])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])C1C=CC=CC=1.[H][H]>[Pd].C(OCC)(=O)C>[C:14]1([CH2:13][CH2:12][C:9]([NH:11][C@H:12]([C:20]([C@@H:22]2[C@H:25]([O:26][C:27](=[O:29])[CH3:28])[N:24]([NH2:30])[C:23]2=[O:31])=[O:21])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 70093171HCID 70093171, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70096544HCID 70096544, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(3S,4S)-3-(N-benzyloxycarbonyl-L-phenylalanyl)-amino-4-acetoxy-azetidin-2-one (1.70 g, 4 mmol) obtained in example 7, was hydrogenated with 3.5 g of 10% palladium on activated carbon in 200 ml of ethyl acetate at 50 psi hydrogen pressure at room temperature for 2 hrs. After removal of catalyst by filtration, the deprotected (3S,4S)-3-(L-phenylalanyl)-amino-4-acetoxy-azetidin-2-one in ethyl acetate was obtained.

Workup

  1. customAfter removal of catalyst
  2. filtrationby filtration

Sources & evidence

ORD record
ord-3d84e2ea17da490893e886c4a787c3ff
Source dataset
uspto-grants-1999_11
Patent number
US05986108

Reaction notes

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