Methanol → Benzyl 7betaamino-2-oxo-3-cephem-4-carboxylate hydrochloride
Reaction equation
O(CC([NH:11][C@@H:12]1[C:30](=[O:31])[N:14]2[C:15]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])=[CH:16][C:17](=[O:19])[S:18][C@H:13]12)=O)C1C=CC=CC=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)[Cl:42].CO>C(Cl)Cl.O>[ClH:42].[NH2:11][C@@H:12]1[C:30](=[O:31])[N:14]2[C:15]([C:20]([O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:21])=[CH:16][C:17](=[O:19])[S:18][C@H:13]12Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -50 °C
Procedure
To a solution of benzyl 7β-(2-phenoxyacetamido)-2-oxo-3-cephem-4-carboxylate (294 mg) in methylene chloride (7 ml) were added successively N,N-dimethylaniline (0.17 ml) and phosphorus pentachloride (281 mg) at -35° C. The mixture was stirred for 1.5 hours at -35° to -30° C. and cooled to -50° C. and then thereto was added methanol (0.57 ml). After the temperature was raised gradually to 0° C. over a period of 1.5 hours, water (0.5 ml) was added. The precipitates were collected by filtration and washed with a small amount of isopropyl alcohol to give benzyl 7β-amino-2-oxo-3-cephem-4-carboxylate hydrochloride (96.5 mg).
Workup
- temperatureAfter the temperature was raised gradually to 0° C. over a period of 1.5 hours
- filtrationThe precipitates were collected by filtration
- washwashed with a small amount of isopropyl alcohol
Sources & evidence
- ORD record
- ord-a964277a71da44ed9cf4d32b043ce8eb
- Source dataset
- uspto-grants-1981_04
- Patent number
- US04264597
Reaction notes
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