Dimethylformamide → HCID 70559797, compound

HRID 443540Notes

Reaction equation

HRID 443540 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-05bad62cebe84cb1ae62b4c992e826a1
Source dataset
uspto-grants-1981_04
Patent number
US04260745

Reaction notes

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