3-Octene → 2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-{2-[(2-methyl-1,3,4-thiadiazol-5-yl)-thio]-prop-1-en-1-yl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide

HRID 463578

反応式

HRID 463578 の反応式
[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[CH:25]=[C:26]([S:28][C:29]1[S:33][C:32]([CH3:34])=[N:31][N:30]=1)[CH3:27])[CH:20]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:19]2=[O:43])=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCC=CCCCC.ClC1C=CC=C(C(OO)=[O:60])C=1>C(Cl)Cl>[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22](=[O:60])[CH2:23][C:24]=1[CH:25]=[C:26]([S:28][C:29]1[S:33][C:32]([CH3:34])=[N:31][N:30]=1)[CH3:27])[CH:20]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:19]2=[O:43])=[O:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 329353-OcteneHCID 70297m-Chloroperbenzoic acidHCID 537695582-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-{2-[(2-methyl-1,3,4-thiadiazol-5-yl)-thio]-prop-1-en-1-yl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

生成物 1

HCID 704857942-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-{2-[(2-methyl-1,3,4-thiadiazol-5-yl)-thio]-prop-1-en-1-yl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of the Z form of 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-{2-[(2-methyl-1,3,4-thiadiazol-5-yl)-thio]-prop-1-en-1-yl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene and -oct-3-ene (0.22 g) in methylene chloride (10 cc) is cooled to 0° C. A solution of 85% pure m-chloroperbenzoic acid (0.07 g) in methylene chloride (5 cc) is added dropwise in the course of 20 minutes. The solution is then stirred for 5 minutes at 0° C., washed with a saturated solution of sodium bicarbonate (20 cc), dried over sodium sulphate and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C. The residue is chromatographed on a column of Merck silica gel (0.06-0.2) (4 g) (diameter of the column: 1 cm; height: 10 cm). Elution is carried out with a 60/40 (by volume) ethyl acetate/cyclohexane mixture (100 cc) and and 3 cc fractions are collected. Fractions 11 to 22 are concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C. This yields the Z form of 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-{2-[(2-methyl-1,3,4-thiadiazol-5-yl)-thio]-prop-1-en-1-yl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide (0.12 g) in the form of a hard white foam.

後処理

  1. washwashed with a saturated solution of sodium bicarbonate (20 cc)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C
  4. customThe residue is chromatographed on a column of Merck silica gel (0.06-0.2) (4 g) (diameter of the column
  5. washElution
  6. customare collected
  7. concentrationFractions 11 to 22 are concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C

出典と根拠

ORDレコード
ord-141b21bae5ae44c3a7086bbdfed536fe
出典データセット
uspto-grants-1985_05
特許番号
US04520193

関連ノート

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