Water → 3-Acetylthiomethyl-7-[{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetyl}amino]-ceph-3-eme-4-carboxylic acid

HRID 1395334Notes

Reaction equation

HRID 1395334 reaction equation
C(O[CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:29])[C:19]([C:23]3[N:24]=[C:25]([NH2:28])[S:26][CH:27]=3)=[N:20][O:21][CH3:22])[C:15](=[O:30])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=O)C.[C:31]([O-:34])(=[S:33])[CH3:32].[K+].P(O)(O)([O-])=O.[Na+].O>C(O)=O>[C:31]([S:33][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:29])[C:19]([C:23]3[N:24]=[C:25]([NH2:28])[S:26][CH:27]=3)=[N:20][O:21][CH3:22])[C:15](=[O:30])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:34])[CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 23670855Potassium ethanethioateHCID 23672064Monosodium phosphateHCID 1317115033-Acetoxymethyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

Product 1

HCID 1317117563-Acetylthiomethyl-7-[{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetyl}amino]-ceph-3-eme-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of the syn isomer of 4.55 g of 3-acetoxymethyl-7-[{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetyl}amino]-ceph-3-eme-4-carboxylic acid, 1.7 g of potassium thioacetate, 2 g of deshydrated monosodium phosphate 1.05 g sodium acid carbonate and 20 ml of distilled water was heated at 70° C. for 90 minutes and the mixture was acidified with 2 ml of formic acid and was extracted 4 times with 60 ml of methyl acetate (insolubles vacuum filtered). The organic solution was washed with water and evaporated to dryness. The residue was dissolved in 20 ml of acetone containing 10% of water and 0.5 g of activated carbon were added thereto. The mixture was stirred for 5 minutes and was vacuum filtered and the filter was washed with acetone containing 10% of water. The filter was evaporated to dryness and the residue was treated with absolute ethanol and was vacuum filtered. The product was washed with alcohol and then with ether to obtain 1.9 g of the pure syn isomer of 3-acetylthiomethyl-7-[{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetyl}amino]-ceph-3-eme-4-carboxylic acid which was identical to the product of Example 6.

Workup

  1. extractionwas extracted 4 times with 60 ml of methyl acetate (insolubles vacuum filtered)
  2. washThe organic solution was washed with water
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in 20 ml of acetone containing 10% of water and 0.5 g of activated carbon
  5. additionwere added
  6. filtrationfiltered
  7. washthe filter was washed with acetone containing 10% of water
  8. customThe filter was evaporated to dryness
  9. additionthe residue was treated with absolute ethanol
  10. filtrationfiltered
  11. washThe product was washed with alcohol

Sources & evidence

ORD record
ord-c26d76e7d6b64f59b026d2c057341dce
Source dataset
uspto-grants-1980_05
Patent number
US04202893

Reaction notes

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