Trifluoroacetic acid → HCID 131712919, compound

HRID 1902970Notes

Reaction equation

HRID 1902970 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:47][O:48][CH2:49][C:50]([O:52]C(C)(C)C)=[O:51])[C:15]([NH:17][CH:18]2[C:45](=[O:46])[N:20]3[C:21]([C:42]([OH:44])=[O:43])=[C:22]([CH2:25][S:26][C:27]4[N:31]([CH2:32][CH2:33][NH:34]C(OC(C)(C)C)=O)[N:30]=[N:29][N:28]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1>C1(OC)C=CC=CC=1>[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:47][O:48][CH2:49][C:50]([OH:52])=[O:51])[C:15]([NH:17][CH:18]2[C:45](=[O:46])[N:20]3[C:21]([C:42]([OH:44])=[O:43])=[C:22]([CH2:25][S:26][C:27]4[N:31]([CH2:32][CH2:33][NH2:34])[N:30]=[N:29][N:28]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131712784HCID 131712784, compound

Product 1

HCID 131712919HCID 131712919, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (12.8 ml.) was added portionwise to a chilled suspension of 7-[2-(2-aminothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-[1-(2-tert-butoxycarbonylaminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 3.2 g.) in anisole (3.2 ml.), and stirred at room temperature for 70 minutes. After removing the solvent from the resultant mixture in vacuo, the residue was triturated with diethyl ether. The precipitates were collected by filtration, dried and dissolved in water (40 ml.). The solution was adjusted to pH 4.8 with 10% sodium hydroxide solution under ice-cooling. The solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (trademark: Mitsubishi Chemical Industries Ltd.) and eluted with 20% aqueous isopropyl alcohol. The eluate was concentrated in vacuo and lyophilized to give 7-[2-(2-aminothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-[1-(2-aminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 1.2 g.).

Workup

  1. customAfter removing the solvent from the resultant mixture in vacuo
  2. customthe residue was triturated with diethyl ether
  3. filtrationThe precipitates were collected by filtration
  4. customdried
  5. dissolutiondissolved in water (40 ml.)
  6. temperaturecooling
  7. wash" (trademark: Mitsubishi Chemical Industries Ltd.) and eluted with 20% aqueous isopropyl alcohol
  8. concentrationThe eluate was concentrated in vacuo

Sources & evidence

ORD record
ord-ccd9bf32e9954d86abbd761cb23bef55
Source dataset
uspto-grants-1982_12
Patent number
US04366153

Reaction notes

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