Dimethylformamide → HCID 70559797, compound

HRID 1657737Notes

Reaction equation

HRID 1657737 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:34](=[O:35])[N:12]2[C:13]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:14](O)[CH2:15][S:16][C@H:11]12)=[O:8].CN(C)C=O.P(Cl)(Cl)[Cl:42]>C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:34](=[O:35])[N:12]2[C:13]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:14]([Cl:42])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24387Phosphorus trichlorideHCID 70559796HCID 70559796, compound

Product 1

HCID 70559797HCID 70559797, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4.2 g. of diphenylmethyl 7-[2-(2-thienyl)acetamido]-3-hydroxy-3-cephem-4-carboxylate in 44 ml. of dry dimethylformamide was added 865 mg. of phosphorus trichloride. The mixture was stirred for 1.5 hours at room temperature and was poured into an ethyl acetate 5% aqueous hydrochloric acid mixture. The ethyl acetate layer was evaporated, was washed with 5% hydrochloric acid, water and was dried. The dried solution was concentrated in vacuo and the product crystallized. The 3-chloro ester was filtered, washed with cold ethyl acetate and dried to yield 2.2 g.

Workup

  1. customThe ethyl acetate layer was evaporated
  2. washwas washed with 5% hydrochloric acid, water
  3. customwas dried
  4. concentrationThe dried solution was concentrated in vacuo
  5. customthe product crystallized
  6. filtrationThe 3-chloro ester was filtered
  7. washwashed with cold ethyl acetate
  8. customdried
  9. customto yield 2.2 g

Sources & evidence

ORD record
ord-e0bd7374d28a445281344e45d312a236
Source dataset
uspto-grants-1976_06
Patent number
US03962227

Reaction notes

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