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Sodium Methoxide → HCID 178525026, 화합물

HRID 249599
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HRID 249599 반응식
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
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참가 물질

8

반응물 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, 화합물

생성물 1

HCID 178525026HCID 178525026, 화합물수율 83.6%

시약·촉매·용매 4

HCID 313
Hydrochloric Acid
용매
HCID 887Methanol용매
HCID 962Water용매
HCID 6228Dimethylformamide용매2회

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온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-eab4705af5634e5abc0734bfb84f0d20
출처 데이터셋
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05214037

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