Methanol → HCID 131717473, compound

HRID 655054Notes

Reaction equation

HRID 655054 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C[O-].[Na+].CO.[CH3:13][O:14][C:15]1[CH:55]=[CH:54][C:18]([CH2:19][O:20][C:21]([C:23]2[N:28]3[C:29](=[O:51])[C@@H:30]([NH:31][C:32](=[O:50])[C:33]([C:37]4[N:38]=[C:39]([NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[S:40][CH:41]=4)=[N:34][O:35][CH3:36])[C@H:27]3[S:26][CH2:25][C:24]=2[CH2:52]Cl)=[O:22])=[CH:17][CH:16]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][O:20][C:21]([C:23]2[N:28]3[C:29](=[O:51])[C@@H:30]([NH:31][C:32](=[O:50])[C:33]([C:37]4[N:38]=[C:39]([NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[S:40][CH:41]=4)=[N:34][O:35][CH3:36])[C@H:27]3[S:26][CH2:25][C:24]=2[CH2:52][S:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)=[O:22])=[CH:54][CH:55]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 123160304HCID 123160304, compoundHCID 178418431pyridine-4-thiol

Product 1

HCID 131717473HCID 131717473, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-mercaptopyridine (222 mg; 2 Eq.) in N,N-dimethylformamide (10 ml) keeping at 0° C. is added a solution of sodium methoxide in methanol (1.5 Eq.). To this mixture is added 7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-methoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (2) (652 mg; 1 mMol.), and the mixture is stirred for 10 minutes. The reaction mixture is diluted with ethyl acetate, washed with water, dried, and concentrated under reduced pressure. The residue is purified by silica gel chromatography (toluene:ethyl acetate) to give 7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-methoxyiminoacetamido]-3-(4-pyridyl)thiomethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (3) (708 mg).

Workup

  1. customkeeping at 0° C.
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel chromatography (toluene:ethyl acetate)

Sources & evidence

ORD record
ord-16c04b4d6beb4964b56f82e9cf9bc208
Source dataset
uspto-grants-1992_07
Patent number
US05134138

Reaction notes

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