Diethyl Ether → HCID 12834118, compound

HRID 1764015Notes

Reaction equation

HRID 1764015 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:11](=[O:32])[CH:12]([NH:13][C:14](=[O:31])[CH:15]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[NH:16]C(OC(C3CC3)C)=O)[C@H:4]2[S:3]1.CCOCC>C(O)=O>[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:11](=[O:32])[CH:12]([NH:13][C:14](=[O:31])[CH:15]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[NH2:16])[C@H:4]2[S:3]1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 12834006HCID 12834006, compound

Product 1

HCID 12834118HCID 12834118, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 2-methyl-7-[N-(1-cyclopropylethoxy)carbonyl-2-phenylglycyl]amino-3-cephem-4-carboxylic acid (2.0 g) in formic acid (10 ml) was stirred for 2.5 hours at room temperature. After the reaction was completed, ether (30 ml) was added to the reaction mixture, and the supernatent was removed three times by decantation. Colorless powder was collected by filtration and washed with ether. Thus obtained powder was suspended in a mixture of acetonitrile (15 ml) and water (1 ml), and the suspension was stirred for 1.5 hours under ice-cooling. The precipitate was collected by filtration and dried to give 2-methyl-7-(2-phenylglycyl)amino-3-cephem-4-carboxylic acid (1.13 g), mp 168.5° to 171° C.

Workup

  1. customthe supernatent was removed three times by decantation
  2. filtrationColorless powder was collected by filtration
  3. washwashed with ether
  4. additionThus obtained powder was suspended in a mixture of acetonitrile (15 ml) and water (1 ml)
  5. temperaturecooling
  6. filtrationThe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-186e4c4596304410bb204c0b0318aad0
Source dataset
uspto-grants-1978_09
Patent number
US04113940

Reaction notes

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