Dimethylformamide → HCID 70563596, compound

HRID 1278321Notes

Reaction equation

HRID 1278321 reaction equation
Cl.[NH2:2][CH:3]1[C:24](=[O:25])[N:5]2[C:6]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[O:12])=[C:7]([Cl:10])[CH2:8][S:9][C@H:4]12.[CH3:26][N:27]([CH:29]=O)[CH3:28].P(Cl)(Cl)Cl>C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[ClH:10].[CH3:26][N:27]([CH:29]=[N:2][C@@H:3]1[C:24](=[O:25])[N:5]2[C:6]([C:11]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=3)=[O:12])=[C:7]([Cl:10])[CH2:8][S:9][C@H:4]12)[CH3:28]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 24387Phosphorus trichlorideHCID 703621504-Nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 70563596HCID 70563596, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 12.8 g. (31.5 mmole) of p-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride in 115 ml. of dry DMF were added with stirring 10.4 g (6.5 ml., 72 mmole) of phosphorus trichloride. The reaction mixture was stirred at room temperature for about 2 days and was then dispersed in a mixture of 5% aqueous sodium bicarbonate and ethyl acetate. The organic layer was separated and treated with 1 N hydrochloric acid. The title compound precipitated from solution and was filtered and dried under vacuum. There were obtained 11.3 g. (67% yield) of the salt.

Workup

  1. customThe organic layer was separated
  2. additiontreated with 1 N hydrochloric acid
  3. customThe title compound precipitated from solution
  4. filtrationwas filtered
  5. customdried under vacuum
  6. customThere were obtained 11.3 g

Sources & evidence

ORD record
ord-554ac4b65e7341c2b190ecca38d179e3
Source dataset
uspto-grants-1981_07
Patent number
US04281117

Reaction notes

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