Tetrahydrofuran → Benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate

HRID 1030047Notes

Reaction equation

O1CCCC1.[NH2:6][C:7]1[S:11][N:10]=[C:9]([C:12](=[N:16][O:17][CH3:18])[C:13](Cl)=[O:14])[N:8]=1.Cl.[NH2:20][CH:21]1[C:46](=[O:47])[N:23]2[C:24]([C:30]([O:32][CH:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])=[C:25]([CH2:28][Cl:29])[CH2:26][S:27][C@H:22]12.C(=O)([O-])O.[Na+]>O>[NH2:6][C:7]1[S:11][N:10]=[C:9]([C:12](=[N:16][O:17][CH3:18])[C:13]([NH:20][CH:21]2[C:46](=[O:47])[N:23]3[C:24]([C:30]([O:32][CH:33]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[O:31])=[C:25]([CH2:28][Cl:29])[CH2:26][S:27][C@H:22]23)=[O:14])[N:8]=1

Participants

Conditions

Temperature: -15 °C

Procedure

To a mixed solution of dichlorometahne (1000 ml) and tetrahydrofuran (200 ml) were added 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetyl chloride (syn isomer) (64 g) and benzhydryl 7-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochloride (100 g) at -15° C. The mixture was stirred at -15° C. for one hour. The reaction mixture was poured into ice-cooled water, and neutralized with sodium hydrogencarbonate. The organic layer was separated, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (130.5 g)

Workup

additionThe reaction mixture was poured into ice-
customThe organic layer was separated
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record: ord-c1c02ef0bf34407db52d8df9f92b5597
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05104866

Reaction notes

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