Hydrochloric Acid → HCID 14621694, compound

HRID 1461165Notes

Reaction equation

HRID 1461165 reaction equation
C([NH:3][CH:4]1[C:30](=[O:31])[N:6]2[C:7]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)=[O:19])=[C:8](/[CH:11]=[CH:12]\[C:13]3[N:14]=[N:15][S:16][CH:17]=3)[CH2:9][S:10][C@H:5]12)=O.Cl>CO>[NH2:3][CH:4]1[C:30](=[O:31])[N:6]2[C:7]([C:18]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)=[O:19])=[C:8](/[CH:11]=[CH:12]\[C:13]3[N:14]=[N:15][S:16][CH:17]=3)[CH2:9][S:10][C@H:5]12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14621691HCID 14621691, compound

Product 1

HCID 14621694HCID 14621694, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The said ester (0.6 g, 1.3 mmol) was dissolved in methanol (10 ml). By addition of concentrated hydrochloric acid (0.1 ml) it was stirred at room temperature for 2 hours. After the solvent was distilled off, a small amount of water was added to the residue and aqueous saturated sodium bicarbonate solution was added to adjust to pH 8-9. It was dissolved by addition of ethyl acetate and the oganic layer was separated. The organic layer was dried and the solvent was dissolved off, and the residue was purified by silica gel column chromatography thereby p-methoxybenzyl 7-amino-3-[(Z)-2-(1,2,3-thiadiazol-4-yl)vinyl]-3-cephem-4-carboxylate (0.21 g) was obtained as a yellow powder solid.

Workup

  1. distillationAfter the solvent was distilled off
  2. additiona small amount of water was added to the residue and aqueous saturated sodium bicarbonate solution
  3. additionwas added
  4. dissolutionIt was dissolved by addition of ethyl acetate
  5. customthe oganic layer was separated
  6. customThe organic layer was dried
  7. dissolutionthe solvent was dissolved off
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ec5a2e9f04924194b2d229690007adc4
Source dataset
uspto-grants-1991_12
Patent number
US05073551

Reaction notes

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