Trifluoroacetic acid → HCID 131718948, compound

HRID 1734277Notes

Reaction equation

HRID 1734277 reaction equation
Cl.Cl.[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:43][O:44][CH2:45][C:46]([O:48]C(C)(C)C)=[O:47])[C:10]([NH:12][C@@H:13]2[C:41](=[O:42])[N:15]3[C:16]([C:38]([O-:40])=[O:39])=[C:17]([CH2:20][N+:21]4([CH3:37])[CH2:26][CH2:25][N:24]([C:27](=[O:36])[C:28]5[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([OH:35])[CH:29]=5)[CH2:23][CH2:22]4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>ClCCl.C1(OC)C=CC=CC=1>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:43][O:44][CH2:45][C:46]([OH:48])=[O:47])[C:10]([NH:12][C@@H:13]2[C:41](=[O:42])[N:15]3[C:16]([C:38]([O-:40])=[O:39])=[C:17]([CH2:20][N+:21]4([CH3:37])[CH2:26][CH2:25][N:24]([C:27](=[O:36])[C:28]5[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([OH:35])[CH:29]=5)[CH2:23][CH2:22]4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131718950HCID 131718950, compound

Product 1

HCID 131718948HCID 131718948, compoundYield 28.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a suspension of 7β-[2-(2-aminothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-[1-methyl-4-(3,4-dihydroxybenzoyl)-1-piperazinio]methyl-3-cephem-4-carboxylate dihydrochloride (syn isomer) (1.35 g) in dichloromethane (5.4 ml) and anisole (1.3 ml) was added dropwise trifluoroacetic acid (4 ml) at 25° C. The stirring was continued for 3 hours at the same temperature. The reaction mixture was poured into diisopropyl ether and the resulting precipitates were collected by filtration. The precipitates were dissolved in water and then adjusted to pH 3.0 with aqueous sodium bicarbonate. The resulting solution was subjected to column chromatography on Diaion HP-20 using 15% aqueous isopropyl alcohol as an eluent. The object fractions were lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-[1-methyl-4-(3,4-dihydroxybenzoyl)-1-piperazinio]methyl-3-cephem-4-carboxylate (syn isomer) (320 mg).

Workup

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration
  3. dissolutionThe precipitates were dissolved in water

Sources & evidence

ORD record
ord-d300eb02cebf47ef85f8627937b91c8e
Source dataset
uspto-grants-1996_07
Patent number
US05532354

Reaction notes

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