Sodium Methoxide → HCID 178447401, compound

HRID 1707445Notes

Reaction equation

HRID 1707445 reaction equation
C([S:4][CH2:5][S:6][C:7]1[N:8]=[N:9][NH:10][CH:11]=1)(=O)C.C[O-].[Na+].[C:15]1([CH:21]([O:28][C:29]([C:31]2[N:36]3[C:37](=[O:59])[C@@H:38]([NH:39][C:40](=[O:58])/[C:41](/[C:45]4[N:46]=[C:47]([NH:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[S:48][CH:49]=4)=[CH:42]\[CH2:43][CH3:44])[C@H:35]3[S:34][CH2:33][C:32]=2OS(C)(=O)=O)=[O:30])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O.CO.Cl.O>[C:15]1([CH:21]([O:28][C:29]([C:31]2[N:36]3[C:37](=[O:59])[C@@H:38]([NH:39][C:40](=[O:58])/[C:41](/[C:45]4[N:46]=[C:47]([NH:50][C:51]([O:53][C:54]([CH3:56])([CH3:57])[CH3:55])=[O:52])[S:48][CH:49]=4)=[CH:42]\[CH2:43][CH3:44])[C@H:35]3[S:34][CH2:33][C:32]=2[S:4][CH2:5][S:6][C:7]2[N:8]=[N:9][NH:10][CH:11]=2)=[O:30])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 3

HCID 10942334Sodium MethoxideHCID 883012357beta-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino]-3-methanesulfonyloxy-3-cephem-4-carboxylic acid diphenylmethyl esterHCID 178477162HCID 178477162, compound

Product 1

HCID 178447401HCID 178447401, compoundYield 70%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-acetylthiomethylthio-1,2,3-triazole (230 mg: 1.22 mMol.) in dimethylformamide (6 ml) is dropwise added a 1.26N-sodium methoxide in methanol (1.9 ml) at -60° C., and the mixture is stirred for 20 minutes, mixed with a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino]-3-methanesulfonyloxy-3-cephem-4-carboxylic acid diphenylmethyl ester (740 mg: 1 mMol.) in dimethylformamide (3 ml), and stirred at the same temperature for 40 minutes. The reaction mixture is diluted with 10% hydrochloric acid (2 ml) and water (30 ml) and extracted with ethyl acetate. The extract is washed with water, dried over sodium sulfate, and purified by silica gel chromatography (toluene: ethyl acetate=2:1) to give 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoylamino]-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (553 mg) as colorless foam. Yield: 70%.

Workup

  1. stirringstirred at the same temperature for 40 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materialdried over sodium sulfate
  5. custompurified by silica gel chromatography (toluene: ethyl acetate=2:1)

Sources & evidence

ORD record
ord-82de7460da3747eeb52fe2bb53caecbd
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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