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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
ノート
印刷プレビュー

反応式

HRID 1074360 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23954Silver触媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-acc6f4c2cdfa4042ba76b3489fb6d2fe
出典データセット
uspto-grants-1990_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04973699

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート