HCID 131714080, compound → HCID 178429604, compound

HRID 2412469Notes

Reaction equation

HRID 2412469 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][C:13]1[CH2:14][S:15][C@@H:16]2[CH:27]([NH2:28])[C:26](=[O:29])[N:17]2[C:18]=1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].F[C:31]1[NH:32][CH:33]=[C:34]([CH2:36][CH2:37][NH:38][C:39](=[O:44])[C:40]([F:43])([F:42])[F:41])[N:35]=1>C(#N)C>[CH3:12][C:13]1[CH2:14][S:15][C@@H:16]2[CH:27]([NH:28][C:31]3[NH:32][CH:33]=[C:34]([CH2:36][CH2:37][NH:38][C:39](=[O:44])[C:40]([F:41])([F:42])[F:43])[N:35]=3)[C:26](=[O:29])[N:17]2[C:18]=1[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20]

Participants

4

Reactant 2

HCID 131714080HCID 131714080, compoundHCID 178523244HCID 178523244, compound

Product 1

HCID 178429604HCID 178429604, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of t-butyl 3-methyl-7-aminoceph-3-em-4-carboxylate toluene-p-sulphonate (0.442 g.) and 2-fluoro-4-(2-trifluoroacetylaminoethyl)imidazole (0.45 g.) was stirred in acetonitrile (dried over molecular sieve, 10 ml.) at 70°-75° for 1.5 hours. The mixture was filtered and the filtrate purified on silica gel (500 g.) eluted with methylene chloride containing 1%, 2%, 3%, 4% and finally 5% v/v methanol. The relevant fractions were combined to give t-butyl 3-methyl-7-[4-(2-trifluoroacetylaminoethyl)imidazol-2-yl]aminoceph-3-em-4-carboxylate (0.34 g.) which was used without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate purified on silica gel (500 g.)
  3. washeluted with methylene chloride containing 1%, 2%, 3%, 4% and finally 5% v/v methanol

Sources & evidence

ORD record
ord-4c64dd8ad34b4c0dad2c57dbdd449656
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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