Acetic Acid → HCID 178452985, 화합물

HRID 1707446노트

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HRID 1707446 반응식
[C:1]([S:9][CH2:10][S:11][C:12]1[N:13]=[N:14][NH:15][CH:16]=1)(=O)[C:2]1C=CC=CC=1.[CH3:17][O-:18].[Na+].C1(C(OC([C:36]2[N:41]3[C:42](=[O:82])[C@@H:43]([NH:44][C:45](=[O:81])/[C:46](/[C:68]4[N:69]=[C:70]([NH:73][C:74]([O:76][C:77]([CH3:80])([CH3:79])[CH3:78])=[O:75])[S:71][CH:72]=4)=[N:47]\[O:48][C:49]([C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)[C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C@H:40]3[S:39]CC=2OS(C)(=O)=O)=O)C2C=CC=CC=2)C=CC=CC=1.[C:88](O)(=O)[CH3:89].[CH3:92][OH:93]>CN(C)C=O.O>[C:50]1([CH:17]([O:18][C:92]([C:36]2[N:41]3[C:42](=[O:82])[C@@H:43]([NH:44][C:45](=[O:81])/[C:46](/[C:68]4[N:69]=[C:70]([NH:73][C:74]([O:76][C:77]([CH3:78])([CH3:80])[CH3:79])=[O:75])[S:71][CH:72]=4)=[N:47]\[O:48][C:49]([C:62]4[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=4)([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)[C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C@H:40]3[S:39][CH2:2][C:1]=2[S:9][CH2:10][S:11][C:12]2[N:13]=[N:14][NH:15][CH:16]=2)=[O:93])[C:89]2[CH:88]=[CH:72][CH:68]=[CH:46][CH:45]=2)[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 887MethanolHCID 10260338benzhydryl (6R,7R)-7-[[(2Z)-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-3-methylsulfonyloxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 10942334Sodium MethoxideHCID 178526204HCID 178526204, 화합물

생성물 1

HCID 178452985HCID 178452985, 화합물수율 44%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 4-benzoylthiomethylthio-1,2,3-triazole (150 mg: 0.60 mMol.) in dimethylformamide (3 ml) at -60° C. is added a solution of sodium methoxide in methanol (1.26N: 0.95 ml), and the mixture is stirred for 80 minutes at -50° to -60° C. To the mixture at -70° C. is added a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-methanesulfonyloxy-3-cephem-4-carboxylic acid diphenylmethyl ester (485 mg: 0.5 mMol.) in dimethylformamide (2 ml) and the mixture is stirred at -70° C. for 20 minutes. The reaction mixture is mixed with acetic acid (0.1 ml), diluted with water, and extracted with ethyl acetate. The extract is washed with brine, dried over sodium sulfate, and concentrated. The residue is crystallized from toluene to give 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-(1,2,3-triazol-4-ylthiomethylthio)-3 -cephem-4-carboxylic acid diphenylmethyl ester (227 mg) as colorless crystals. Yield: 44%.

후처리

  1. stirringthe mixture is stirred at -70° C. for 20 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is crystallized from toluene

출처 및 근거

ORD 기록
ord-d687218b1c8543588c2e7fe107660093
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05352792

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