HCID 131712609, compound → HCID 131712608, compound

HRID 1659791Notes

Reaction equation

HRID 1659791 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:46]1[N:47]=[C:48]([NH2:51])[S:49][CH:50]=1)[C:5]([NH:7][CH:8]1[C:44](=[O:45])[N:10]2[C:11]([C:28]([O:30][CH:31]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:29])=[C:12]([CH2:15][O:16][C:17](=[O:27])[C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=3)[CH2:13][S:14][C@H:9]12)=[O:6]>C(O)C.O1CCCC1>[CH3:1][O:2][N:3]=[C:4]([C:46]1[N:47]=[C:48]([NH2:51])[S:49][CH:50]=1)[C:5]([NH:7][CH:8]1[C:44](=[O:45])[N:10]2[C:11]([C:28]([O:30][CH:31]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:29])=[C:12]([CH2:15][O:16][C:17](=[O:27])[C:18]3[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

4

Reactant 1

HCID 131712609HCID 131712609, compound

Product 1

HCID 131712608HCID 131712608, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Platinic oxide (0.4 g.) was added to a solution of benzhydryl 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(4-nitrobenzoyloxymethyl)-3-cephem-4-carboxylate (syn isomer) (4.3 g.) in a mixture of ethanol (50 ml.) and tetrahydrofuran (50 ml.), and the suspension was subjected to catalytic reduction at ambient temperature under ordinary pressure for 3 hours. After removing the catalyst from the resultant mixture by filtration, the filtrate was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and the solution was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The residue was pulverized with diethyl ether to give benzhydryl 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(4-aminobenzoyl-oxymethyl)-3-cephem-4-carboxylate (syn isomer) (3.0 g.).

Workup

  1. customAfter removing the catalyst from the resultant mixture
  2. filtrationby filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-64edef6a734148d1bb79c4c907fb2278
Source dataset
uspto-grants-1981_12
Patent number
US04304770

Reaction notes

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