Formic Acid → HCID 131711505, compound

HRID 261980Notes

Reaction equation

HRID 261980 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:50])[C:19]([C:25]3[N:26]=[C:27]([NH:30]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:28][CH:29]=3)=[N:20][O:21][CH2:22][CH:23]=[CH2:24])[C:15](=[O:51])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2].C(O)=O>O>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:50])[C:19]([C:25]3[N:26]=[C:27]([NH2:30])[S:28][CH:29]=3)=[N:20][O:21][CH2:22][CH:23]=[CH2:24])[C:15](=[O:51])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 131711504HCID 131711504, compound

Product 1

HCID 131711505HCID 131711505, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 610 mg of the product of Example 8 and 3 ml of 50% aqueous formic acid was heated at 60° C. for 15 minutes and 4 ml of water were added. The mixture was stirred and vacuum filtered. The filtrate was rinsed with water and concentrated to dryness under reduced pressure. The residue was taken up in water and was effloresced. The mixture was vacuum filtered and the product was rinsed to obtain 120 mg of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-(2-propenyl) oxyiminoacetamido]-ceph-3-eme-4-carboxylic acid with a melting point of about 160° C. and a syn configuration.

Workup

  1. filtrationvacuum filtered
  2. washThe filtrate was rinsed with water
  3. concentrationconcentrated to dryness under reduced pressure
  4. filtrationfiltered
  5. washthe product was rinsed

Sources & evidence

ORD record
ord-76b43029be4949dfa36f0549c9452630
Source dataset
uspto-grants-1979_05
Patent number
US04152432

Reaction notes

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