Water → Benzhydryl 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)-acetamido]-3-[2-(2-pyridyl)vinyl]-3-cephem-4-carboxylate

HRID 980987Notes

Reaction equation

HRID 980987 reaction equation
[NH2:1][CH:2]1[C:33](=[O:34])[N:4]2[C:5]([C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])=[C:6]([CH:9]=[CH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[CH2:7][S:8][C@H:3]12.C[Si](C)(C)NC(=O)C.[CH2:43]([O:45][N:46]=[C:47]([C:51]1[N:55]=[C:54]([NH2:56])[S:53][N:52]=1)[C:48](Cl)=[O:49])[CH3:44].O>C(OCC)(=O)C.O1CCCC1>[CH2:43]([O:45][N:46]=[C:47]([C:51]1[N:55]=[C:54]([NH2:56])[S:53][N:52]=1)[C:48]([NH:1][CH:2]1[C:33](=[O:34])[N:4]2[C:5]([C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])=[C:6]([CH:9]=[CH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[CH2:7][S:8][C@H:3]12)=[O:49])[CH3:44]

Participants

7

Reactant 4

HCID 962WaterHCID 25989Acetamide, N-(trimethylsilyl)-HCID 543507512-(5-Amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetyl chlorideHCID 131714364Benzhydryl 7-amino-3-[2-(2-pyridyl)vinyl]-3-cephem-4-carboxylate

Product 1

HCID 131715050Benzhydryl 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)-acetamido]-3-[2-(2-pyridyl)vinyl]-3-cephem-4-carboxylateYield 90.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of benzhydryl 7-amino-3-[2-(2-pyridyl)-vinyl]-3-cephem-4-carboxylate (trans isomer) (25 g) and N-(trimethylsilyl)acetamide (4.2 g) in ethyl acetate (20 ml) and tetrahydrofuran (10 ml) was stirred at ambient temperature for 20 minutes to give a clear solution. To the solution was added 2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)-acetylchloride (syn isomer) (1.4 g) at -15°~-20° C. and stirred at the same temperature for 30 minutes. Water (20 ml) was added to the resulting solution, and the separated organic layer was washed with 5% aqueous sodium bicarbonate and brine, dried over magnesium sulfate and evaporated to give benzhydryl 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)-acetamido]-3-[2-(2-pyridyl)vinyl]-3-cephem-4-carboxylate (syn isomer) (trans isomer) (3.6 g).

Workup

  1. customto give a clear solution
  2. stirringstirred at the same temperature for 30 minutes
  3. washthe separated organic layer was washed with 5% aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-78455888739a48b1812e41cdf183082c
Source dataset
uspto-grants-1987_01
Patent number
US04639448

Reaction notes

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