Ethanol → HCID 131713255, compound

HRID 904916Notes

Reaction equation

HRID 904916 reaction equation
[N:1]([CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:15]([NH:16][C:17](=[O:28])[C:18]([C:22]3[N:23]=[C:24]([NH2:27])[S:25][CH:26]=3)=[N:19][O:20][CH3:21])[C:14](=[O:29])[N:9]2[C:10]=1[C:11]([OH:13])=[O:12])=[N+:2]=[N-:3].C([O-])(=O)C.[Na+:34].C(O)C>CO>[N:1]([CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:15]([NH:16][C:17](=[O:28])[C:18]([C:22]3[N:23]=[C:24]([NH2:27])[S:25][CH:26]=3)=[N:19][O:20][CH3:21])[C:14](=[O:29])[N:9]2[C:10]=1[C:11]([O-:13])=[O:12])=[N+:2]=[N-:3].[Na+:34]

Participants

5

Reactant 3

HCID 702EthanolHCID 517045Sodium AcetateHCID 131713256HCID 131713256, compound

Product 1

HCID 131713255HCID 131713255, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of the product of Example 3 and 5 ml of a molar solution of sodium acetate in methanol was stirred and was vacuum filtered to recover a brown solid. The fltrate was added to 1 ml of ethanol and was vacuum filtered to remove a second insoluble. The solid phases were added to 5 ml of ethanol and the mixture was vacuum filtered. The filtrate was evaporated to dryness and the residue was taken up in a little ethanol to obtain a second crop which was added to 2 ml of methanol. 5 ml of ethanol were added thereto and the mixture was vacuum filtered. The filtrate was evaporated to dryness and the residue was triturated with a little absolute ethanol to obtain 0.4 g of the syn isomer of sodium 3-azidomethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylate.

Workup

  1. filtrationfiltered
  2. customto recover a brown solid
  3. additionThe fltrate was added to 1 ml of ethanol
  4. filtrationfiltered
  5. customto remove a second insoluble
  6. additionThe solid phases were added to 5 ml of ethanol
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customto obtain a second crop which
  10. filtrationfiltered
  11. customThe filtrate was evaporated to dryness
  12. customthe residue was triturated with a little absolute ethanol

Sources & evidence

ORD record
ord-2cced0ed960444148f5826bea352d2bf
Source dataset
uspto-grants-1983_12
Patent number
US04420478

Reaction notes

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