Formic Acid → Benzhydryl 7-formamido-3-hydroxycepham-4-carboxylate

HRID 704259Notes

Reaction equation

[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[NH2:11][CH:12]1[C:36](=[O:37])[N:14]2[CH:15]([C:20]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH:16]([OH:19])[CH2:17][S:18][C@H:13]12.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:1]([NH:11][CH:12]1[C:36](=[O:37])[N:14]2[CH:15]([C:20]([O:22][CH:23]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[CH:16]([OH:19])[CH2:17][S:18][C@H:13]12)=[O:2]

Participants

Conditions

Temperature: 3 °C

Procedure

Formic acid (0.4 ml) and acetic anhydride (1 ml) were stirred at 40° C. for 30 minutes. The reaction mixture was cooled in an ice-water bath and added dropwise to a mixture of benzhydryl 7-amino-3-hydroxycepham-4-carboxylate (1.0 g) in methylene chloride (30 ml) at 3° C. The mixture was stirred at 3° C. for 10 minutes and adjusted to pH 7.0 with 5% aqueous solution of sodium bicarbonate, washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give benzhydryl 7-formamido-3-hydroxycepham-4-carboxylate (1.05 g) as powder.

Workup

temperatureThe reaction mixture was cooled in an ice-water bath
washwashed with water
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record: ord-624f8c5376b544588acf02caa1b7a678
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04985555

Reaction notes

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