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Sodium Chloride → benzhydryl 7beta-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate

HRID 1074360
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HRID 1074360 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[CH:7]=[CH:8]\[SH:9])[CH:2]=1.[I-].[Na+].[CH:12]1([O:15][N:16]=[C:17]([C:48]2[N:49]=[C:50]([NH:53][CH:54]=[O:55])[S:51][CH:52]=2)[C:18]([NH:20][C@@H:21]2[C:46](=[O:47])[N:23]3[C:24]([C:30]([O:32][CH:33]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:31])=[C:25]([CH2:28]Cl)[CH2:26][S:27][C@H:22]23)=[O:19])[CH2:14][CH2:13]1.[Cl-].[Na+]>C(#N)C.[Ag].C(OCC)(=O)C>[CH:12]1([O:15][N:16]=[C:17]([C:48]2[N:49]=[C:50]([NH:53][CH:54]=[O:55])[S:51][CH:52]=2)[C:18]([NH:20][C@@H:21]2[C:46](=[O:47])[N:23]3[C:24]([C:30]([O:32][CH:33]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:31])=[C:25]([CH2:28][S:9]/[CH:8]=[CH:7]\[C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[CH2:26][S:27][C@H:22]23)=[O:19])[CH2:14][CH2:13]1
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참가 물질

8

반응물 4

HCID 5234Sodium ChlorideHCID 5238Sodium IodideHCID 14705800(Z)-2-(3-pyridyl)ethenethiolHCID 131716070Benzhydryl 7beta-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate

생성물 1

HCID 131716064benzhydryl 7beta-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate
수율 60.2%

시약·촉매·용매 3

HCID 23954Silver촉매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

A mixture of silver salt of (Z)-2-(3-pyridyl)ethenethiol (2.03 g) and sodium iodide (3.36 g) in acetonitrile (40 ml) was stirred for 20 minutes at 0° C. in the dark. To the mixture was added benzhydryl 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (2.03 g) at -20° C., and the mixture was stirred at 0° C. for 1.5 hours. The mixture was poured into a mixture of saturated aqueous solution of sodium chloride (200 ml) and ethyl acetate (100 ml). The insoluble material was filtered off and the organic layer was separated. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with diethyl ether to give benzhydryl 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[(Z)-2-(3-pyridyl)vinylthiomethyl]-3-cephem-4-carboxylate (syn isomer) (1.41 g).

후처리

  1. stirringthe mixture was stirred at 0° C. for 1.5 hours
  2. filtrationThe insoluble material was filtered off
  3. customthe organic layer was separated
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-acc6f4c2cdfa4042ba76b3489fb6d2fe
출처 데이터셋
uspto-grants-1990_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04973699

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