t-Butyl 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylate → HCID 178503660, compound

HRID 2412495Notes

Reaction equation

HRID 2412495 reaction equation
C(OCC1[CH2:7][S:8][C@@H]2C(N)C(=O)N2C=1C(OC(C)(C)C)=O)(=O)C.[C:23]([O:26][CH2:27][C:28]1[CH2:29][S:30][C@@H:31]2[CH:42]([NH:43][C:44]3[NH:45][CH:46]=[C:47]([CH2:49]OC)[N:48]=3)[C:41](=[O:52])[N:32]2[C:33]=1[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])(=[O:25])[CH3:24]>>[C:23]([O:26][CH2:27][C:28]1[CH2:29][S:30][C@@H:31]2[CH:42]([NH:43][C:44]3[NH:45][CH:46]=[C:47]([CH2:49][S:8][CH3:7])[N:48]=3)[C:41](=[O:52])[N:32]2[C:33]=1[C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])(=[O:25])[CH3:24]

Participants

3

Reactant 2

HCID 15573429t-Butyl 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylateHCID 178494613HCID 178494613, compound

Product 1

HCID 178503660HCID 178503660, compound

Procedure

4-Chloromethyl-2-fluoro-1-triphenylmethylimidazole was treated with methanethiol and triethylamine in THF solution to give 2-fluoro-4-methylthiomethyl-1-triphenylmethylimidazole. This was condensed with t-butyl 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylate as for the starting material of Example 42 to give t-butyl 3-acetoxymethyl-7-(4-methylthiomethylimidazol-2-yl)aminoceph-3-em-4-carboxylate, having the following n.m.r. spectrum in d6DMSO: 1.5 (s, 9H); 2.0 (s, 6H); 3.5 (d, 2H); 3.8 (d, 2H); 4.7 (d, 1H); 5.0 (d, 1H); 5.25 (d, 1H); 5.65 (d, 1H); 7.0 (s, 1H).

Sources & evidence

ORD record
ord-cfbbbdfedb04494ba922753853014312
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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