Trifluoroacetic acid → HCID 131717696, compound

HRID 2380299Notes

Reaction equation

HRID 2380299 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:33][O:34][CH2:35][C:36]([O:38]C(C)(C)C)=[O:37])[C:8]([NH:10][C@@H:11]2[C:31](=[O:32])[N:13]3[C:14]([C:28]([O-:30])=[O:29])=[C:15]([CH2:18][N+:19]4[N:23]5[CH2:24][CH2:25][CH2:26][NH:27][C:22]5=[CH:21][CH:20]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.FC(F)(F)C(O)=O.C(OCC)(=O)C>C(Cl)Cl.C1(OC)C=CC=CC=1>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:33][O:34][CH2:35][C:36]([OH:38])=[O:37])[C:8]([NH:10][C@@H:11]2[C:31](=[O:32])[N:13]3[C:14]([C:28]([O-:30])=[O:29])=[C:15]([CH2:18][N+:19]4[N:23]5[CH2:24][CH2:25][CH2:26][NH:27][C:22]5=[CH:21][CH:20]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 131717698HCID 131717698, compound

Product 1

HCID 131717696HCID 131717696, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a suspension of 7β-[2-(2-aminothiazol-4-yl)-2-t-butoxycarbonylmethoxyiminoacetamido]-3-(4,5,6,7-tetrahydro-1-pyrazolo[1,5-a]pyrimidinio)methyl-3-cephem-4-carboxylate (syn isomer) (800 mg) in methylene chloride (2.4 ml) and anisole (0.8 ml) was added dropwise trifluoroacetic acid (1.6 ml) at 20° C. The stirring was continued for 3 hours at the room temperature. The reaction mixture was poured into ethyl acetate. The resulting precipitates were collected by filtration. The precipitates were dissolved in water (50 ml) and the mixture was adjusted to pH 6.5 with a saturated aqueous solution of sodium bicarbonate. The solution was subjected to column chromatography on HP-20 using water as an eluent and the object fractions were adjusted to pH 2.0 with 1N hydrochloric acid. The resulting solution was subjected to column chromatography on HP-20 using 15% aqueous isopropyl alcohol as an eluent and the object fractions were lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-carboxymethoxyiminoacetamido]- 3-(4,5,6,7-tetrahydro-1-pyrazolo[1,5-a]pyrimidinio)methyl-3-cephem-4-carboxylate (syn isomer) (300 mg).

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. dissolutionThe precipitates were dissolved in water (50 ml)

Sources & evidence

ORD record
ord-b62dde2f5c4348b7bdd73f373d8cd7af
Source dataset
uspto-grants-1994_11
Patent number
US05366970

Reaction notes

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