Formic Acid → HCID 131718127, compound

HRID 5524Notes

Reaction equation

HRID 5524 reaction equation
C(O)=O.FC(F)(F)C(O)=O.Cl.[NH2:12][C:13]1[S:17][N:16]=[C:15]([C:18](=[N:49][O:50][CH2:51][C:52]([OH:54])=[O:53])[C:19]([NH:21][C@@H:22]2[C:47](=[O:48])[N:24]3[C:25]([C:44]([O-:46])=[O:45])=[C:26]([CH2:29][N+:30]4([CH3:43])[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]4)[CH2:27][S:28][C@H:23]23)=[O:20])[N:14]=1>C(OCC)(=O)C>[NH2:12][C:13]1[S:17][N:16]=[C:15]([C:18](=[N:49][O:50][CH2:51][C:52]([OH:54])=[O:53])[C:19]([NH:21][C@@H:22]2[C:47](=[O:48])[N:24]3[C:25]([C:44]([O-:46])=[O:45])=[C:26]([CH2:29][N+:30]4([CH3:43])[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]4)[CH2:27][S:28][C@H:23]23)=[O:20])[N:14]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 6422Trifluoroacetic acidHCID 131718129HCID 131718129, compound

Product 1

HCID 131718127HCID 131718127, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of formic acid (10 ml) and trifluoroacetic acid (5 ml) was added 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-(1-methyl-4-tert-butoxycarbonyl-1-piperazinio)methyl-3-cephem-4-carboxylate hydrochloride (syn isomer) (5.7 g) at 20° C. under stirring. The stirring was continued for 1.5 hours at the same temperature. The reaction mixture was poured into ethyl acetate (200 ml). The resulting precipietes were collected by filtration, added to water. The mixture was adjusted to pH 2.0 with a saturated aqueous solution of sodium bicarbonate and filtered. The filtrate was subjected to column chromatography on Diaion HP-20 using 10% aqueous isopropanol as an eluent. The eluate was evaporated in vacuo to remove isopropanol and then lyophilized to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-(1-methyl-1-piperazinio)methyl-3-cephem-4-carboxylate (syn isomer) (1.50 g).

Workup

  1. filtrationThe resulting precipietes were collected by filtration
  2. additionadded to water
  3. filtrationfiltered
  4. customThe eluate was evaporated in vacuo
  5. customto remove isopropanol

Sources & evidence

ORD record
ord-cc6c87b9be304b508b4408d695432fd7
Source dataset
uspto-grants-1993_09
Patent number
US05244890

Reaction notes

Loading…