Trifluoroacetic acid → HCID 88179237, compound

HRID 992701Notes

Reaction equation

HRID 992701 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:62]/[O:63]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)/[C:27]([NH:29][C@@H:30]2[C:60](=[O:61])[N:32]3[C:33]([C:44]([O:46]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:45])=[C:34]([S:37][C:38]4[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=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>C1(OC)C=CC=CC=1>[NH2:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:62]/[OH:63])/[C:27]([NH:29][C@@H:30]2[C:60](=[O:61])[N:32]3[C:33]([C:44]([OH:46])=[O:45])=[C:34]([S:37][C:38]4[CH:39]=[CH:40][N:41]=[CH:42][CH:43]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 88179846HCID 88179846, compound

Product 1

HCID 88179237HCID 88179237, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

To a suspension of diphenylmethyl 7β-[2-(2-tritylaminothiazol-4-yl)-2-(Z)-(trityloxyimino)acetamido]-3-(4-pyridylthio)-3-cephem-4-carboxylate (1.37 g, 1.21 m mol) in anisole (2.7 ml) was added trifluoroacetic acid (5.4 ml) at 5° C. and the resulting solution was stirred at room temperature for 4 hours. The mixture was poured into IPE (150 ml) and the precipitates were collected by filtration, washed with IPE and dried in vacuo. The powder was dissolved in water (100 ml) by addition of saturated NaHCO3 aqueous solution. The solution was adjusted to pH 6 by addition of 1N HCl and chromatographed on HP-20 (50 ml) and eluted with 10% aqueous IPA. The eluent was lyophilized and the crude product was purified by preparative HPLC to give 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(hydroxyimino)acetamido]-3-(4-pyridylthio)-3-cephem-4-carboxylic acid (52 mg).

Workup

  1. additionThe mixture was poured into IPE (150 ml)
  2. filtrationthe precipitates were collected by filtration
  3. washwashed with IPE
  4. customdried in vacuo
  5. dissolutionThe powder was dissolved in water (100 ml) by addition of saturated NaHCO3 aqueous solution
  6. additionThe solution was adjusted to pH 6 by addition of 1N HCl
  7. customchromatographed on HP-20 (50 ml)
  8. washeluted with 10% aqueous IPA
  9. customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-4d575d0d127745909e68cede1b9ba987
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

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