Methanol → HCID 131717476, compound

HRID 655059Notes

Reaction equation

HRID 655059 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:73]=[CH:72][C:18]([CH2:19][O:20][C:21]([C:23]2[N:28]3[C:29](=[O:69])[C@@H:30]([NH:31][C:32](=[O:68])[C:33]([C:55]4[N:56]=[C:57]([NH:60][C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])[S:58][CH:59]=4)=[N:34][O:35][C:36]([C:39]([O:41][CH:42]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[O:40])([CH3:38])[CH3:37])[C@H:27]3[S:26][CH2:25][C:24]=2[CH2:70]Cl)=[O:22])=[CH:17][CH:16]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:13][O:14][C:15]1[CH:73]=[CH:72][C:18]([CH2:19][O:20][C:21]([C:23]2[N:28]3[C:29](=[O:69])[C@@H:30]([NH:31][C:32](=[O:68])[C:33]([C:55]4[N:56]=[C:57]([NH:60][C:61]([O:63][C:64]([CH3:65])([CH3:67])[CH3:66])=[O:62])[S:58][CH:59]=4)=[N:34][O:35][C:36]([C:39]([O:41][CH:42]([C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=4)[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[O:40])([CH3:37])[CH3:38])[C@H:27]3[S:26][CH2:25][C:24]=2[CH2:70][S:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)=[O:22])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 1317174757beta-[2-(2-t-Butoxycarbonylamino-4-thiazolyl)-2-(1-diphenylmethoxycarbonyl-1-methylethoxyimino)acetamido]-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl esterHCID 178418431pyridine-4-thiol

Product 1

HCID 131717476HCID 131717476, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-mercaptopyridine (178 mg; 2 Eq.) in N,N-di-methylformamide (10 ml) at 0° C. are added a solution of sodium methoxide in methanol (1.5 Eq.) and then 7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-(1-diphenylmethoxycarbonyl-1-methylethoxyimino)acetamido]-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (2) (712 mg; 0.8 mMol.), and the mixture is stirred for 15 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-(1-diphenylmethoxycarbonyl-1-methylethoxyimino)acetamido]-3-(4-pyridyl)thiomethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (3) (497 mg).

Workup

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

Sources & evidence

ORD record
ord-b3a07e35bcf04b999153c0918bdcf33c
Source dataset
uspto-grants-1992_07
Patent number
US05134138

Reaction notes

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