HCID 18705564, compound → N-[1,2-Dihydro-1-[1-hydroxy-2-(hydroxymethyl)-4-oxo-3-azetidinyl]-2-oxo-4-pyrimidinyl]benzamide

HRID 361871Notes

Reaction equation

HRID 361871 reaction equation
C([O:8][N:9]1[CH:12]([CH2:13][O:14]CC2C=CC=CC=2)[CH:11]([N:22]2[CH:37]=[CH:36][C:26]([NH:27][C:28](=[O:35])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:25][C:23]2=[O:24])[C:10]1=[O:38])C1C=CC=CC=1.[H][H]>CO.[Ni]>[OH:8][N:9]1[CH:12]([CH2:13][OH:14])[CH:11]([N:22]2[CH:37]=[CH:36][C:26]([NH:27][C:28](=[O:35])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:25][C:23]2=[O:24])[C:10]1=[O:38]

Participants

5

Reactant 2

HCID 18705564HCID 18705564, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18705563N-[1,2-Dihydro-1-[1-hydroxy-2-(hydroxymethyl)-4-oxo-3-azetidinyl]-2-oxo-4-pyrimidinyl]benzamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1-N-Benzyloxy-3-(N-benzoylcytosin-1-yl)-4-benzyloxymethyl-2-azetidinone (10mmole) is taken up in methanol (50 ml) and hydrogenated using Raney nickel (5 g) and hydrogen at a pressure of 40 psi for 6 hours. The reaction mixture is filtered, the catalyst washed with methanol (20 ml) and the combined fractions are concentrated to afford the product as a solid.

Workup

  1. customfor 6 hours
  2. filtrationThe reaction mixture is filtered
  3. washthe catalyst washed with methanol (20 ml)
  4. concentrationthe combined fractions are concentrated

Sources & evidence

ORD record
ord-6d81a1f289a340c1b1ca7b060b1f259b
Source dataset
uspto-grants-1999_02
Patent number
US05866691

Reaction notes

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