Acetonitrile → HCID 13848572, compound

HRID 482844Notes

Reaction equation

HRID 482844 reaction equation
C(OC([N:11]([CH:22]1[CH2:25][N:24]([CH:26]([C:30]2[S:31][CH:32]=[CH:33][CH:34]=2)[C:27]([OH:29])=[O:28])[C:23]1=[O:35])[C:12](=[O:21])[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH2:14])=O)C1C=CC=CC=1.[H][H].C(OCC)(=O)C.C(#N)C>CO.[Pd].O>[C:15]1([CH:13]([C:12]([NH:11][CH:22]2[CH2:25][N:24]([CH:26]([C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:27]([OH:29])=[O:28])[C:23]2=[O:35])=[O:21])[NH2:14])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 20243622HCID 20243622, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13848572HCID 13848572, compoundYield 14.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-[3-(N-Benzyloxycarbonyl-2-phenylglycinamido)-2-oxo-1-azetidinyl]-2-(2-thienyl)acetic acid (0.19 g.) was dissolved in methanol (10 ml.), and to the solution, there was added 10% palladium on carbon (0.15 g.) as a catalyst. The mixture was subjected to catalytic reduction in a stream of hydrogen gas at ordinary temperature and ordinary pressure. A calculated volume of hydrogen gas was absorbed into the mixture in the course of 6.5 hours. The catalyst was filtered off from the reaction mixture and the filtrate was evaporated to dryness under reduced pressure to give an oily residue, which was pulverized with ethyl acetate. The powder (0.09 g.) obtained was treated with a mixture of acetonitrile and water (volume ratio, 20:1) to give 2-[3-(2-phenylglycinamido)-2-oxo-1-azetidinyl]-2-(2-thienyl)acetic acid (0.02 g.).

Workup

  1. customA calculated volume of hydrogen gas was absorbed into the mixture in the course of 6.5 hours
  2. filtrationThe catalyst was filtered off from the reaction mixture
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. customto give an oily residue, which
  5. customThe powder (0.09 g.) obtained

Sources & evidence

ORD record
ord-c42c528cccd7440c975588957b09f14e
Source dataset
uspto-grants-1986_03
Patent number
US04576753

Reaction notes

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