Ethanol → Sodium 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylate

HRID 27965Notes

Reaction equation

HRID 27965 reaction equation
C([O-])(=O)C.[Na+:5].C(O)C.[C:9]([O:12][CH2:13][C:14]1[CH2:15][S:16][C@@H:17]2[CH:24]([NH:25][C:26](=[O:37])[C:27]([C:31]3[N:32]=[C:33]([NH2:36])[S:34][CH:35]=3)=[N:28][O:29][CH3:30])[C:23](=[O:38])[N:18]2[C:19]=1[C:20]([OH:22])=[O:21])(=[O:11])[CH3:10]>O>[C:9]([O:12][CH2:13][C:14]1[CH2:15][S:16][C@@H:17]2[CH:24]([NH:25][C:26](=[O:37])[C:27]([C:31]3[N:32]=[C:33]([NH2:36])[S:34][CH:35]=3)=[N:28][O:29][CH3:30])[C:23](=[O:38])[N:18]2[C:19]=1[C:20]([O-:22])=[O:21])(=[O:11])[CH3:10].[Na+:5]

Participants

5

Reactant 3

HCID 702Ethanol3×HCID 517045Sodium AcetateHCID 1317115033-Acetoxymethyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

Product 1

HCID 131711736Sodium 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 6 g of sodium acetate in 20 ml of water was added with stirring at 20° C. to 50 ml of 98% ethanol and with continued stirring 25 g of an ethanol solvate of the syn isomer of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid were added thereto. After dissolution occured, the solution was cooled to 0° C. and 50 ml of 98% ethanol were added thereto dropwise with stirring. Activated carbon was added to the solution which was then filtered and the filtrate was heated to 20° C. Crystallization spontaneously occured shortly thereafter and filtration by aspiration was effected at room temperature 16 hours later. The recovered product was washed with a 1-7 water-ethanol mixture, with ethanol and then with ether to obtain colorless crystals of the D form of the syn isomer of sodium 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4 -carboxylate which after drying under reduced pressure contained 4.8% of water (by Fischer). The spectrum of X-ray diffraction and the infrared spectrum in nujol confirmed the D form.

Workup

  1. additionwere added
  2. dissolutionAfter dissolution
  3. additionActivated carbon was added to the solution which
  4. filtrationwas then filtered
  5. temperaturethe filtrate was heated to 20° C
  6. customCrystallization
  7. filtrationfiltration by aspiration
  8. washThe recovered product was washed with a 1-7 water-ethanol mixture, with ethanol

Sources & evidence

ORD record
ord-9341e2414a574b8db0e08b4d43382356
Source dataset
uspto-grants-1980_09
Patent number
US04224371

Reaction notes

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