HCID 12834157, compound → HCID 12834062, compound

HRID 851599Notes

Reaction equation

HRID 851599 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:11](=[O:33])[CH:12]([NH:13][C:14](=[O:32])[CH:15]([C:24]3[CH:29]=[CH:28][C:27]([S:30][CH3:31])=[CH:26][CH:25]=3)[NH:16]C(OC(C)(C)C)=O)[C@H:4]2[S:3]1>C(O)=O>[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:11](=[O:33])[CH:12]([NH:13][C:14](=[O:32])[CH:15]([C:24]3[CH:29]=[CH:28][C:27]([S:30][CH3:31])=[CH:26][CH:25]=3)[NH2:16])[C@H:4]2[S:3]1

Participants

3

Reactant 1

HCID 12834157HCID 12834157, compound

Product 1

HCID 12834062HCID 12834062, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 2-methyl-7-[N-(tert.-butoxycarbonyl)-2-(4-methylthiophenyl)glycyl]amino-3-cephem-4-carboxylic acid (3.0 g) in formic acid (100 ml) was stirred for 1 hour under anhydrous condition at room temperature. After the reaction was completed, the solvent was removed from the reaction mixture under reduced pressure, and the residue was dissolved in a mixture of water and ethyl acetate, after which the aqueous layer was separated. The aqueous layer was washed with ethyl acetate, and the organic solvent was completely removed under reduced pressure. The insoluble material was collected by filtration and lyophilized to give white powder of 2-methyl-7-[2-(4-methylthiophenyl)glycyl]amino-3-cephem-4-carboxylic acid (1.2 g), mp 165° to 175° C.

Workup

  1. customthe solvent was removed from the reaction mixture under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of water and ethyl acetate
  3. customafter which the aqueous layer was separated
  4. washThe aqueous layer was washed with ethyl acetate
  5. customthe organic solvent was completely removed under reduced pressure
  6. filtrationThe insoluble material was collected by filtration

Sources & evidence

ORD record
ord-e17e74edbbb148b1a527199431bfbd01
Source dataset
uspto-grants-1983_05
Patent number
US04385176

Reaction notes

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