Methanesulfonyl chloride → HCID 178480383、化合物

HRID 1614079ノート

反応式

HRID 1614079 の反応式
CS(Cl)(=O)=O.[NH2:6][C:7]1[S:8][CH:9]=[C:10]([C:12](=[N:16][O:17][CH:18]2[CH2:21][S:20][CH2:19]2)[C:13]([OH:15])=O)[N:11]=1.C(N(C(C)C)CC)(C)C.[NH2:31][C@@H:32]1[C:49](=[O:50])[N:34]2[C:35]([C:46]([O-:48])=[O:47])=[C:36]([CH2:39][N+:40]3[N:41]([CH3:45])[CH:42]=[CH:43][CH:44]=3)[CH2:37][S:38][C@H:33]12.C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C>CN(C)C=O.O1CCCC1.C(OCC)C>[NH2:6][C:7]1[S:8][CH:9]=[C:10]([C:12](=[N:16][O:17][CH:18]2[CH2:21][S:20][CH2:19]2)[C:13]([NH:31][C@@H:32]2[C:49](=[O:50])[N:34]3[C:35]([C:46]([O-:48])=[O:47])=[C:36]([CH2:39][N+:40]4[N:41]([CH3:45])[CH:42]=[CH:43][CH:44]=4)[CH2:37][S:38][C@H:33]23)=[O:15])[N:11]=1

参加物

9

反応物 5

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 543232982-(2-Aminothiazol-4-yl)-2-(3-thietanyloxyimino)acetic acidHCID 178480378HCID 178480378、化合物

生成物 1

HCID 178480383HCID 178480383、化合物収率 24.5%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methanesulfonyl chloride (0.61 ml) was added to a solution of 2-(2-aminothiazol-4-yl)-2-(3-thietanyloxyimino)acetic acid (syn isomer, 0.99 g) and N,N-diisopropyl-N-ethylamine (1.33 ml) in N,N-dimethylformamide (20 ml) at -55° to -50° C., and the mixture was stirred for 10 minutes to produce an activated acid solution. To a solution of bis(trisfluoroacetic acid) salts of 7β-amino-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (2 g) and N,O-bis(trimethylsilyl)acetamide (3.79 ml) in tetrahydrofuran (20 ml) was added the above activated acid solution under ice-cooling, and the reaction mixture was stirred at the same temperature for an hour. The resultant mixture was poured into diethyl ether, and the precipitates were collected by filtration. The precipitates were suspended in water (20 ml), and the suspension was adjusted to pH 5 with 5% aqueous solution of sodium bicarbonate and subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark, manufactured by Mitsubishi Chemical Industries) and eluted with 10% aqueous solution of isopropyl alcohol. The fractions containing the object compound were collected, evaporated in vacuo to remove isopropyl alcohol, and lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-(3-thietanyloxyimino)acetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (syn isomer, 0.5 g).

後処理

  1. customto produce an activated acid solution
  2. temperaturecooling
  3. stirringthe reaction mixture was stirred at the same temperature for an hour
  4. filtrationthe precipitates were collected by filtration
  5. wash" (Trademark, manufactured by Mitsubishi Chemical Industries) and eluted with 10% aqueous solution of isopropyl alcohol
  6. additionThe fractions containing the object compound
  7. customwere collected
  8. customevaporated in vacuo
  9. customto remove isopropyl alcohol

出典と根拠

ORDレコード
ord-4c27ef5de5c3487e9491ac4c345723dc
出典データセット
uspto-grants-1993_03
特許番号
US05194432

反応ノート

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