Diethyl Ether → HCID 12834118, compound

HRID 851595Notes

Reaction equation

HRID 851595 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]([CH:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]3=C=O)[NH:16]OC(C3CC3)C)[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:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH2:16])[C@H:4]2[S:3]1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 131712995HCID 131712995, 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-caboxylic 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-ed9a643fb1114fa8be2582c941b210e0
Source dataset
uspto-grants-1983_05
Patent number
US04385176

Reaction notes

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