(3S-trans)-3-[[[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-4-methyl-1-(phenylmethoxy)-2-azetidinone → (3S-trans)-3-[[[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-1-hydroxy-4-methyl-2-azetidinone

HRID 1156739Notes

Reaction equation

HRID 1156739 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]([NH:11][CH:12]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:13]([NH:15][C@H:16]2[C@H:19]([CH3:20])[N:18]([O:21]CC3C=CC=CC=3)[C:17]2=[O:29])=[O:14])=[O:10])[C:5](=[O:36])[C:4]1=[O:37])[CH3:2]>C(O)C.[Pd]>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]([NH:11][CH:12]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:13]([NH:15][C@H:16]2[C@H:19]([CH3:20])[N:18]([OH:21])[C:17]2=[O:29])=[O:14])=[O:10])[C:5](=[O:36])[C:4]1=[O:37])[CH3:2]

Participants

4

Reactant 1

HCID 13036845(3S-trans)-3-[[[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-4-methyl-1-(phenylmethoxy)-2-azetidinone

Product 1

HCID 56621498(3S-trans)-3-[[[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-1-hydroxy-4-methyl-2-azetidinone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(3S-trans)-3-[[[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]phenylacetyl]amino]-4-methyl-1-(phenylmethoxy)-2-azetidinone (0.270 g) is dissolved in ethanol (25 ml) and hydrogenated over 10% palladium on charcoal catalyst (130 mg) for two hours. The reaction mixture is filtered and concentrated to a solid (0.220 g).

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated to a solid (0.220 g)

Sources & evidence

ORD record
ord-7cbc2e887b24458c95a2677962dac59e
Source dataset
uspto-grants-1982_06
Patent number
US04337197

Reaction notes

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