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Ethyl Acetate → 1-(Cyclohexyloxycarbonyloxy)Ethyl 7beta-[2-(2-Aminothiazol-4-Yl)Acetamido]-3-Acetoacetoxymethylceph-3-Em-4-Carboxylate

HRID 892924
ノート
印刷プレビュー

反応式

HRID 892924 の反応式
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][C@@H:11]2[C:29](=[O:30])[N:13]3[C:14]([C:26]([O-:28])=[O:27])=[C:15]([CH2:18][O:19][C:20](=[O:25])[CH2:21][C:22]([CH3:24])=[O:23])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].[C:32](=[O:44])([O:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)[O:33][CH:34](I)[CH3:35].C(OCC)(=O)C>CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][C@@H:11]2[C:29](=[O:30])[N:13]3[C:14]([C:26]([O:28][CH:34]([O:33][C:32]([O:37][CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)=[O:44])[CH3:35])=[O:27])=[C:15]([CH2:18][O:19][C:20](=[O:25])[CH2:21][C:22]([CH3:24])=[O:23])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=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

5

反応物 3

HCID 8857Ethyl AcetateHCID 111092781-Iodoethyl cyclohexyl carbonateHCID 131715451Sodium 7beta-[2-(2-aminothiazol-4-yl)acetamido]-3-acetoacetoxymethyl-ceph-3-em-4-carboxylate

生成物 1

HCID 1317174261-(Cyclohexyloxycarbonyloxy)Ethyl 7beta-[2-(2-Aminothiazol-4-Yl)Acetamido]-3-Acetoacetoxymethylceph-3-Em-4-Carboxylate収率 52.9%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
-5 °C

実験手順

In 30 ml of N,N-dimethylformamide is dissolved 4.76 g of sodium 7β-[2-(2-aminothiazol-4-yl]acetamido]-3-acetoacetoxymethylceph-3-em-4-carboxylate and the solution is cooled to -5° C. With stirring, to the solution is added dropwise 5.0 g of 1-iodoethyl cyclohexyl carbonate, followed by stirring for further 5 minutes. The reaction mixture is poured into a mixture of 300 ml of ethyl acetate and 200 ml of ice water and the organic layer is separated. The aqueous layer is extracted with 200 ml of ethyl acetate. The organic layers are combined and washed with 150 ml each portion of ice water (three times) and saturated aqueous sodium chloride (three times) and then dried over anhydrous magnesium sulfate. The solution is then distilled off under reduced pressure and isopropyl ether is added to the residue. The resultant white powder is collected by filtration, washed with isopropyl ether and dried to obtain 3.3 g of the title compound.

後処理

  1. stirringby stirring for further 5 minutes
  2. customthe organic layer is separated
  3. extractionThe aqueous layer is extracted with 200 ml of ethyl acetate
  4. washwashed with 150 ml each portion of ice water (three times) and saturated aqueous sodium chloride (three times)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solution is then distilled off under reduced pressure and isopropyl ether
  7. additionis added to the residue
  8. filtrationThe resultant white powder is collected by filtration
  9. washwashed with isopropyl ether
  10. customdried

出典と根拠

ORDレコード
ord-5ca26217271f40bab34e5766ff77128d
出典データセット
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05120841

反応ノート

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