Trifluoroacetic acid → HCID 178502776, compound

HRID 974871Notes

Reaction equation

HRID 974871 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:64]/[O:65][CH3:66])/[C:27]([NH:29][CH:30]2[C:62](=[O:63])[N:32]3[C:33]([C:46]([O:48]C(C4C=CC=CC=4)C4C=CC=CC=4)=[S:47])=[C:34]([C:37]4[O:38][C:39]5[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=5[N:41]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>C1(OC)C=CC=CC=1>[NH2:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:64]/[O:65][CH3:66])/[C:27]([NH:29][CH:30]2[C:62](=[O:63])[N:32]3[C:33]([C:46]([OH:48])=[S:47])=[C:34]([C:37]4[O:38][C:39]5[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=5[N:41]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 172974451O-benzhydryl (6R)-3-(1,3-benzoxazol-2-yl)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbothioate

Product 1

HCID 178502776HCID 178502776, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

A 272 mg portion of diphenylmethyl 7-{(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido }-3-(benzoxazol-2-yl)thio-3-cephem-4-carboxylate was dissolved in 1.4 ml of anisole. Under cooling on an ice bath, the resulting solution was mixed with 2.7 ml of trifluoroacetic acid and stirred for 30 minutes at the same temperature. The resulting reaction mixture was added dropwise to 14 ml of diisopropyl ether, and the formed precipitate was recovered by filtration and dried. The thus dried product was suspended in 3 ml of distilled water, and the suspension was adjusted to pH 7 with saturated sodium bicarbonate aqueous solution. Thereafter, this solution was chromatographed using 10 ml of HP-20 resin and freeze-dried to obtain 73 mg of the title compound as a sodium salt (yield, 46%).

Workup

  1. temperatureUnder cooling on an ice bath
  2. customThe resulting reaction mixture
  3. filtrationthe formed precipitate was recovered by filtration
  4. customdried
  5. customThereafter, this solution was chromatographed
  6. customfreeze-dried

Sources & evidence

ORD record
ord-926b3650fe394946bc52804a86bef27e
Source dataset
uspto-grants-1997_03
Patent number
US05607927

Reaction notes

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