Sodium Acetate → HCID 131712375, compound

HRID 1758717Notes

Reaction equation

HRID 1758717 reaction equation
[CH3:1][C:2]1[S:6][C:5]([S:7][CH2:8][C:9]2[CH2:10][S:11][C@@H:12]3[CH:19]([NH:20][C:21](=[O:35])[C:22]([C:29]4[N:30]=[C:31]([NH2:34])[S:32][CH:33]=4)=[N:23][O:24][CH2:25][C:26]([OH:28])=[O:27])[C:18](=[O:36])[N:13]3[C:14]=2[C:15]([OH:17])=[O:16])=[N:4][N:3]=1.C([O-])(=O)C.[Na+:41]>CO>[CH3:1][C:2]1[S:6][C:5]([S:7][CH2:8][C:9]2[CH2:10][S:11][C@@H:12]3[CH:19]([NH:20][C:21](=[O:35])[C:22]([C:29]4[N:30]=[C:31]([NH2:34])[S:32][CH:33]=4)=[N:23][O:24][CH2:25][C:26]([OH:28])=[O:27])[C:18](=[O:36])[N:13]3[C:14]=2[C:15]([O-:17])=[O:16])=[N:4][N:3]=1.[Na+:41].[Na+:41].[CH3:1][C:2]1[S:6][C:5]([S:7][CH2:8][C:9]2[CH2:10][S:11][C@@H:12]3[CH:19]([NH:20][C:21](=[O:35])[C:22](=[N:23][O:24][CH2:25][C:26]([OH:28])=[O:27])[C:29]4[N:30]=[C:31]([NH2:34])[S:32][CH:33]=4)[C:18](=[O:36])[N:13]3[C:14]=2[C:15]([O-:17])=[O:16])=[N:4][N:3]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 131712376HCID 131712376, compound

Product 1

HCID 131712375HCID 131712375, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

0.1 g of animal black was added at room temperature to a stirred solution of 1.1 g of the product of Example 7, 25 ml of methanol and 7.7 ml of a solution of sodium acetate in methanol and the mixture was vacuum filtered. The filter was rinsed with methanol and the filtrate was evaporated under reduced pressure at less than 30° C. to a volume of about 5 ml. 50 ml of pure ethanol were added thereto at room temperature and the mixture was stirred at 20°-25° C. for 15 minutes and was vacuum filtered. The product was rinsed 3 times with 5 ml of pure ethanol and 3 times with 10 ml of ether and was dried under reduced pressure to obtain 0.965 g of the syn isomer of disodium 3-[(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl]-7-[2-(2-amino-4-thiazolyl)-2-(carboxymethyloxyimino)-acetamido]-ceph-3-eme-4-carboxylate with a specific rotation of [α] D20 =-55.5°±1.5° (c=1% in water).

Workup

  1. filtrationfiltered
  2. washThe filter was rinsed with methanol
  3. customthe filtrate was evaporated under reduced pressure at less than 30° C. to a volume of about 5 ml
  4. addition50 ml of pure ethanol were added
  5. filtrationfiltered
  6. washThe product was rinsed 3 times with 5 ml of pure ethanol and 3 times with 10 ml of ether
  7. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-f06b4547c22f404981efc586dd5a0af9
Source dataset
uspto-grants-1983_02
Patent number
US04374834

Reaction notes

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