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(#N)C>[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
Conditions
- Temperature
- 10 °C
Procedure
Chlorine gas was bubbled into a mixture of 7.9 ml (30 mmol) of triphenyl phosphite in 45 ml of acetonitrile at -10° C. Because the mixture solidified it was allowed to warm to 10° C. whence the reaction mixture again liquified. The addition of chlorine gas was continued until a yellow color persisted in the mixture. Then 0.1 ml of triphenyl phosphite was added to decolorize th solution (about 30.4 mmol of the triphenyl phosphite-chlorine kinetic compound was formed). To this solution was added 5.4 gm (10 mmol) of 4'-nitrobenzyl 7-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylate. Thereafter 2.42 ml (30 mmol) of pyridine in 8 ml of acetonitrile was added dropwise over a 30 minute period with the temperature of the reaction mixture at 0° to 10° C. After stirring the reaction mixture for 1 hour, the cooling bath was removed, and the reaction mixture was allowed to stir at room temperature for 90 minutes. Then 9.25 ml (100 mmol) of isobutanol was added. After 90 minutes at room temperature the reaction mixture was filtered to provide 0.95 gm (23.4%) of the titled nucleus ester hydrochloride: m.p. 186° C. (dec.).
Sources & evidence
- ORD record
- ord-1635c83c34964e8eb4b6483e0540897e
- Source dataset
- uspto-grants-1980_10
- Patent number
- US04226986
Reaction notes
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