1,3-Bis(trimethylsilyl)urea → Benzhydryl 7-[2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-mesyloxy-3-cephem-4-carboxylate

HRID 2351127ノート

反応式

HRID 2351127 の反応式
[NH2:1][CH:2]1[C:30](=[O:31])[N:4]2[C:5]([C:14]([O:16][CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[C:6]([O:9][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:7][S:8][C@H:3]12.C[Si](NC(N[Si](C)(C)C)=O)(C)C.Cl.[CH2:45]([O:48][N:49]=[C:50]([C:54]1[N:58]=[C:57]([NH2:59])[S:56][N:55]=1)[C:51](Cl)=[O:52])[CH:46]=[CH2:47].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[CH2:45]([O:48][N:49]=[C:50]([C:54]1[N:58]=[C:57]([NH2:59])[S:56][N:55]=1)[C:51]([NH:1][CH:2]1[C:30](=[O:31])[N:4]2[C:5]([C:14]([O:16][CH:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:15])=[C:6]([O:9][S:10]([CH3:13])(=[O:11])=[O:12])[CH2:7][S:8][C@H:3]12)=[O:52])[CH:46]=[CH2:47]

参加物

7

反応物 4

HCID 875621,3-Bis(trimethylsilyl)ureaHCID 516892Sodium BicarbonateHCID 736584962-Allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride hydrochlorideHCID 88528619Benzhydryl 7-amino-3-mesyloxy-3cephem-4-carboxylate

生成物 1

HCID 131716147Benzhydryl 7-[2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-mesyloxy-3-cephem-4-carboxylate収率 92.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of benzhydryl 7-amino-3-mesyloxy-3cephem-4-carboxylate (6.91 g) and bis(trimethylsilyl)-urea (18.4 g) in methylene chloride (69 ml) was added 2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetyl chloride hydrochloride (syn isomer) (4.08 g) at -10° C. under stirring and the mixture was stirred at the same temperature for 30 minutes. After the reaction mixture was added to a stirred mixture of water and methylene chloride, the solution was adjusted to pH 7.0 with a saturated aqueous solution of sodium bicarbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give benzhydryl 7-[2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-mesyloxy-3-cephem-4-carboxylate (syn isomer) (8.90 g).

後処理

  1. stirringthe mixture was stirred at the same temperature for 30 minutes
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

出典と根拠

ORDレコード
ord-205fbaa6eb344f8d8d8375c9f6f6cc02
出典データセット
uspto-grants-1989_10
特許番号
US04871730

反応ノート

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