Sodium Acetate → HCID 131712373, compound

HRID 1758715Notes

Reaction equation

HRID 1758715 reaction equation
[CH3:1][N:2]1[C:6]([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:5][N:4]=[N:3]1.C([O-])(=O)C.[Na+:41]>CO>[CH3:1][N:2]1[C:6]([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:5][N:4]=[N:3]1.[Na+:41].[Na+:41].[CH3:1][N:2]1[C:6]([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:5][N:4]=[N:3]1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 131712374HCID 131712374, compound

Product 1

HCID 131712373HCID 131712373, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

0.15 g of animal black were added at room temperature to a solution of 1.35 g of the product of Example 4, 9.7 ml of a molar solution of sodium acetate in methanol and 28 ml of methanol containing 10% water and the mixture was stirred and vacuum filtered. The product was rinsed 3 times with 1 ml of methanol containing 10% water and 3 times with 5 ml of methanol. The filtrate was concentrated under reduced pressure at less than 30° C. to a volume of 10 ml and 50 ml of ethanol were slowly added thereto at 20°-25° C. The suspension was stirred for 15 minutes at room temperature and was vacuum filtered. The product was rinsed 3 times with 5 ml of ethanol and 3 times with 10 ml of ether and was dried under reduced pressure to obtain 1.05 g of the syn isomer of disodium 3-[(1-methyl-tetrazol-5-yl)-thiomethyl]-7-[2-(2-amino-4-thiazolyl)-2-(carboxymethyloxyimino)-acetamido]-ceph-3-eme-4-carboxylate with a specific rotation of [α]D20 =-16.5°±1° (c=1% in water).

Workup

  1. filtrationvacuum filtered
  2. washThe product was rinsed 3 times with 1 ml of methanol containing 10% water and 3 times with 5 ml of methanol
  3. concentrationThe filtrate was concentrated under reduced pressure at less than 30° C. to a volume of 10 ml and 50 ml of ethanol
  4. additionwere slowly added
  5. customat 20°-25° C
  6. stirringThe suspension was stirred for 15 minutes at room temperature
  7. filtrationfiltered
  8. washThe product was rinsed 3 times with 5 ml of ethanol and 3 times with 10 ml of ether
  9. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-2a59601f060e4efe8f47ed3355fa3366
Source dataset
uspto-grants-1983_02
Patent number
US04374834

Reaction notes

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