Trifluoroacetic acid → HCID 131713920, compound

HRID 1632757Notes

Reaction equation

HRID 1632757 reaction equation
C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.[NH2:16][C:17]1[S:18][CH:19]=[C:20]([C:22](=[N:46][O:47][CH3:48])[C:23]([NH:25][CH:26]2[C:44](=[O:45])[N:28]3[C:29]([C:33]([O:35][CH2:36][C:37]([O:39]C(C)(C)C)=[O:38])=[O:34])=[CH:30][CH2:31][S:32][C@H:27]23)=[O:24])[N:21]=1>C(OC(C)C)(C)C>[NH2:16][C:17]1[S:18][CH:19]=[C:20]([C:22](=[N:46][O:47][CH3:48])[C:23]([NH:25][CH:26]2[C:44](=[O:45])[N:28]3[C:29]([C:33]([O:35][CH2:36][C:37]([OH:39])=[O:38])=[O:34])=[CH:30][CH2:31][S:32][C@H:27]23)=[O:24])[N:21]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131713915HCID 131713915, compound

Product 1

HCID 131713920HCID 131713920, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

To a solution of anisole (5 ml) and trifluoroacetic acid (6 ml) was added tert-butoxycarbonylmethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 1.5 g) with stirring at ambient temperature. The reaction mixture was stirred for an hour at the same temperature. Then the resultant solution was dropwise added to diisopropyl ether (150 ml). The precipitates were collected by filtration and washed with diisopropyl ether. The precipitates were dissolved in an aqueous solution of sodium bicarbonate. The aqueous solution was adjusted to pH 2.5 with conc. hydrochloric acid. The precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide under reduced pressure to give carboxymethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 0.85 g), IR and NMR spectra of which were the same as those of the object compound of Example 14.

Workup

  1. stirringThe reaction mixture was stirred for an hour at the same temperature
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with diisopropyl ether
  4. dissolutionThe precipitates were dissolved in an aqueous solution of sodium bicarbonate
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with water
  7. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-92b7a0d1261e4a89aeb5da3da3d16bed
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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