HCID 141560620, compound → HCID 88496648, compound

HRID 893759Notes

Reaction equation

HRID 893759 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:69]/[O:70]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)/[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>FC(F)(F)C(O)=O.C(OC(C)C)(C)C>[NH2:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:69]/[OH:70])/[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

4

Reactant 1

HCID 141560620HCID 141560620, compound

Product 1

HCID 88496648HCID 88496648, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7914Diisopropyl EtherSolvent

Procedure

Diphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(E)-(5,6-dihydroxybenzimidazol-1-yl)-1-propen-1-yl]-3-cephem-4-carboxylate (XIb) (125 mg was dissolved in trifluoroacetic acid (TFA, 1.2 ml), stirred at room temperature for an hour and diluted with isopropyl ether to precipitate 63 mg of a crude product. The product was chromatographed on a column of Prep C18 (Waters) with water and 5% acetonitrile in water as eluants. The desired fractions, checked by HPLC*, were combined, concentrated to a small volume and freeze-dried to afford 7 mg (13% yield) of the title compound.

Workup

  1. customto precipitate 63 mg of a crude product
  2. customThe product was chromatographed on a column of Prep C18 (Waters) with water and 5% acetonitrile in water as eluants
  3. concentrationconcentrated to a small volume
  4. customfreeze-dried

Sources & evidence

ORD record
ord-bf657a56de0f42aea0c673f0cf685ebe
Source dataset
uspto-grants-1992_06
Patent number
US05126336

Reaction notes

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