Triphenyl phosphite → HCID 70457302, compound
Reaction equation
[Cl:1][Cl:2].[P:3]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(Cl)Cl>[P:3]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1.[Cl:1][Cl:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Chlorine gas was bubbled into a solution of 2.63 ml (10 mmol) of triphenyl phosphite in 50 ml of methylene chloride at 0° to 5° C. until a yellow color was obtained. The excess chlorine, evidenced by the yellow color of the solution, was dissipated by adding triphenyl phosphite dropwise until the yellow color was discharged. This required an additional 0.47 ml (1.8 mmol) giving a solution of 11.8 mmol of the triphenyl phosphite-chlorine kinetic compound. To this solution were added 5.04 gm (10 mmol) of 4-nitrobenzyl 7-phenoxyacetamido-3-chloro-3-cephem-4-carboxylate and a solution of 1.01 ml (12.5 mmol) of pyridine in 2 ml of methylene chloride. With the addition of the pyridine solution the temperature of the reaction mixture rose from 5° to 12° C. The solution was then allowed to stir at room temperature for 2 hours after which time was added 5.1 ml (55 mmol) of isobutanol. Within 10 minutes the title nucleus ester hydrochloride began to crystallize from the reaction mixture. After 11/2 hours the mixture was filtered to provide, after drying, 3.71 gm (91.4%) of the title product as nearly white crystals: m.p. 180°-181° C. (dec.).
Workup
- customwas obtained
Sources & evidence
- ORD record
- ord-91ffc6f6012e42f5bd1f3c6710ae88ef
- Source dataset
- uspto-grants-1980_07
- Patent number
- US04211702
Reaction notes
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