Trifluoroacetic acid → HCID 88496366, compound

HRID 893760Notes

Reaction equation

HRID 893760 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:69]/[O:70][CH3:71])/[C:27]([NH:29][CH:30]2[C:67](=[O:68])[N:32]3[C:33]([C:51]([O:53]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:52])=[C:34](/[CH:37]=[CH:38]/[CH2:39][N:40]4[C:44]5[CH:45]=[C:46]([OH:50])[C:47]([OH:49])=[CH:48][C:43]=5[N:42]=[CH: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.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(OC(C)C)(C)C>[NH2:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:69]/[O:70][CH3:71])/[C:27]([NH:29][CH:30]2[C:67](=[O:68])[N:32]3[C:33]([C:51]([OH:53])=[O:52])=[C:34](/[CH:37]=[CH:38]/[CH2:39][N:40]4[C:44]5[CH:45]=[C:46]([OH:50])[C:47]([OH:49])=[CH:48][C:43]=5[N:42]=[CH:41]4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 88496478HCID 88496478, compound

Product 1

HCID 88496366HCID 88496366, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

A mixture of diphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[(E)-3-(5,6-dihydroxybenzimidazol-1-yl)-1-propen-1-yl]-3-cephem-4-carboxylate (XIn) (171 mg, 0.175 mmol), anisole (0.5 ml) and TFA (4 ml) was stirred for an hour at room temperature. The mixture was diluted with isopropyl ether to precipitate a crude product. The product was chromatographed on a column of Prep C18 (Waters, 20×300 mm), and the column was eluted successively with 10% MeOH/H2O, 15% MeOH/H2O and 25% MeOH/H2O. The eluate was monitored by UV absorption at 254 nm and the fractions showing UV absorption were further checked by HPLC.*The fractions containing the desired product were combined and concentrated in vacuo. The concentrate was freeze-dried to give 52 mg (52% yield) of the title product.

Workup

  1. customto precipitate a crude product
  2. customThe product was chromatographed on a column of Prep C18 (Waters, 20×300 mm)
  3. washthe column was eluted successively with 10% MeOH/H2O, 15% MeOH/H2O and 25% MeOH/H2O
  4. customThe eluate was monitored by UV absorption at 254 nm
  5. customUV absorption
  6. additioncontaining the desired product
  7. concentrationconcentrated in vacuo
  8. customThe concentrate was freeze-dried

Sources & evidence

ORD record
ord-48f70f359f8a469da0614fc5cd7cf614
Source dataset
uspto-grants-1992_06
Patent number
US05126336

Reaction notes

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