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Sodium Methoxide → HCID 178525026, compound

HRID 249599
Notes
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Reaction equation

HRID 249599 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:61])[C@@H:38](NC(=O)/C(/C4N=C(NC(OC(C)(C)C)=O)SC=4)=N\OCC=C)[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:61])[CH2:38][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:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 10942334Sodium MethoxideHCID 88301273benzhydryl (6R,7R)-7-[[(2Z)-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-prop-2-enoxyiminoacetyl]amino]-3-methylsulfonyloxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 178477162HCID 178477162, compound

Product 1

HCID 178525026HCID 178525026, compoundYield 83.6%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-78 °C

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 at the same temperature for 25 minutes, and cooled to -78° C. To the reaction mixture is dropwise added a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol -4-yl)-2-(2-propenyloxyimino)acetamido]-3 methanesulfonyloxy-3-cephem-4-carboxylic acid diphenylmethyl ester (770 mg : 1 mMol.) in dimethylformamide (3 ml), and the mixture is stirred at the same temperature for 40 minutes. The reaction mixture is diluted with 1N-hydrochloric acid (2 ml) and water (50 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). The eluted material is crystallized from toluene to give 7β-](Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl) 2-(2propentyloxyimino)acetamido]-3-(1,2,3-triazol-4-ylthiomethylthio) -3-cephem-4- carboxylic acid diphenylmethyl ester (415 mg) as colorless crystals. Yield : 51%. mp. 167° to 170° C. (decomposition).

Workup

  1. stirringthe mixture is stirred 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)
  6. customThe eluted material is crystallized from toluene

Sources & evidence

ORD record
ord-eab4705af5634e5abc0734bfb84f0d20
Source dataset
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05214037

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes