Phosphorus trichloride → HCID 88686871, compound

HRID 1249427Notes

Reaction equation

HRID 1249427 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:36](=[O:37])[N:11]2[C:12]([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])=[C:13](/[CH:17]=[CH:18]/[Cl:19])[CH2:14][S:15](=O)[C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)Cl>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH:9]1[C:36](=[O:37])[N:11]2[C:12]([C:20]([O:22][CH:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:21])=[C:13](/[CH:17]=[CH:18]/[Cl:19])[CH2:14][S:15][C@H:10]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 88686893HCID 88686893, compound

Product 1

HCID 88686871HCID 88686871, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzhydryl 7-t-butoxycarbonylamino-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylate-1-oxide (7.3 g) in N,N-dimethylformamide (35 ml) was added phosphorus trichloride (1.76 ml) at -40° C. After stirring at the same temperature for 30 minutes, the mixture was poured into ice-water. The resulting precipitate was collected by filtration and dried to give benzhydryl 7-t-butoxycarbonylamino-3-[(E)-2-chlorovinyl]-3-cephem-4-carboxylate (6.3 g).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-cc8bc1f4a5b34306a304cd24c31040d9
Source dataset
uspto-grants-1986_12
Patent number
US04631274

Reaction notes

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