Pyridine → HCID 13785492, compound

HRID 1905801Notes

Reaction equation

HRID 1905801 reaction equation
[C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH:25]C(=O)CC4C=CC=CC=4)[C@H:21]3[S:20][CH2:19][CH:18]2[O:36][S:37]([C:40]2[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=2)(=[O:39])=[O:38])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl>ClCCl.CO>[C:8]1([CH:7]([O:14][C:15]([CH:17]2[N:22]3[C:23](=[O:35])[C@@H:24]([NH2:25])[C@H:21]3[S:20][CH2:19][CH:18]2[O:36][S:37]([C:40]2[CH:41]=[CH:42][C:43]([CH3:46])=[CH:44][CH:45]=2)(=[O:39])=[O:38])=[O:16])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 13785486HCID 13785486, compound

Product 1

HCID 13785492HCID 13785492, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-30 °C

Procedure

To a solution of 3-p-toluenesulfonyloxy-7beta-phenylacetylaminocepham-4-carboxylic acid diphenylmethyl ester (3d) in dichloromethane (7 parts) cooling at -25° to -20° C. under nitrogen are added pyridine (2 equivalents) and phosphorus pentachloride (1.7 equivalents). After stirring at -15° to -10° C. for 4 hours, the mixture is diluted with methanol (12 parts) cooled at -30° C., stirred at -30° to -25° C. for 30 minutes and at 0° to 5° C. for 2 hours. The reaction mixture is diluted with dichloromethane and ice-water and stirred at 0° to 5° C. for 20 minutes. The formed organic layer is taken, washed with water, dried, and concentrated. The residue is crystallized from dichloromethane-ether mixture to give 3-p-toluenesulfonyloxy-7beta-aminocepham-4-carboxylic acid diphenylmethyl ester (4d) p-toluenesulfonate salt. mp. 190°-194° C. (decomposition).

Workup

  1. stirringstirred at -30° to -25° C. for 30 minutes and at 0° to 5° C. for 2 hours
  2. stirringstirred at 0° to 5° C. for 20 minutes
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is crystallized from dichloromethane-ether mixture

Sources & evidence

ORD record
ord-2338a421927b44db9497182b69588905
Source dataset
uspto-grants-1987_03
Patent number
US04647658

Reaction notes

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