Hydrochloric Acid → Pivaloyloxymethyl 7-(imidazol-2-yl)amino-3-methylceph-3-em-4-carboxylate hydrochloride

HRID 1463168Notes

Reaction equation

HRID 1463168 reaction equation
[CH3:1][C:2]1[CH2:3][S:4][C@@H:5]2[CH:20]([NH2:21])[C:19](=[O:22])[N:6]2[C:7]=1[C:8]([O:10][CH2:11][O:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[O:9].[ClH:23].F[C:25]1[NH:26][CH:27]=[CH:28][N:29]=1.Cl>CN(C=O)C.C(#N)C.CO>[ClH:23].[NH:26]1[CH:27]=[CH:28][N:29]=[C:25]1[NH:21][CH:20]1[C:19](=[O:22])[N:6]2[C:7]([C:8]([O:10][CH2:11][O:12][C:13](=[O:18])[C:14]([CH3:15])([CH3:16])[CH3:17])=[O:9])=[C:2]([CH3:1])[CH2:3][S:4][C@H:5]12

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 126246272-Fluoro-1H-imidazole hydrochlorideHCID 12877764Pivaloyloxymethyl 3-methyl-7-aminoceph-3-em-4-carboxylate

Product 1

HCID 70509486Pivaloyloxymethyl 7-(imidazol-2-yl)amino-3-methylceph-3-em-4-carboxylate hydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 0.18 g. of pivaloyloxymethyl 3-methyl-7-aminoceph-3-em-4-carboxylate (0.18 g.) and 2-fluoroimidazole hydrochloride (0.14 g.) in DMF (1 ml.) and acetonitrile (1 ml.) was heated at 50° for 7 hours. After evaporation the residue was chromatographed on silica gel using CH2Cl2 /MeOH 95:5 v/v as eluant. The oily product was treated with one equivalent of HCl in MeOH. The solution was evaporated and the residue was triturated with ether and filtered to give pivaloyloxymethyl 7-(imidazol-2-yl)amino-3-methylceph-3-em-4-carboxylate hydrochloride having the following n.m.r. in d6DMSO+CD3COOD: 1.2 (s, 9H); 2.1 (s, 3H); 3.6 (m, 2H); 5.25 (d, 1H); 5.7 (d, 1H); 5.85 (m, 2H); 7.05 (s, 2H).

Workup

  1. customAfter evaporation the residue
  2. customwas chromatographed on silica gel
  3. customThe solution was evaporated
  4. customthe residue was triturated with ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-ea4f6338e54e442da6553f0adaab9aed
Source dataset
uspto-grants-1984_07
Patent number
US04463173

Reaction notes

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