3-Octene → 3-Acetonyl-2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide

HRID 463586

反応式

HRID 463586 の反応式
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([C:16]1[CH2:23][S:22][CH:21]2[N:18]([C:19](=[O:56])[CH:20]2[NH:24][C:25](=[O:55])[C:26](=[N:52][O:53][CH3:54])[C:27]2[N:28]=[C:29]([NH:32][C:33]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[S:30][CH:31]=2)[C:17]=1[C:57]([O:59][CH:60]([C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)=[O:58])[C:13]([CH3:15])=[O:14].CCC=CCCCC.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:12]([C:16]1[CH2:23][S:22](=[O:9])[CH:21]2[N:18]([C:19](=[O:56])[CH:20]2[NH:24][C:25](=[O:55])[C:26](=[N:52][O:53][CH3:54])[C:27]2[N:28]=[C:29]([NH:32][C:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[S:30][CH:31]=2)[C:17]=1[C:57]([O:59][CH:60]([C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)[C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1)=[O:58])[C:13]([CH3:15])=[O:14]

参加物

6

反応物 4

HCID 329353-OcteneHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 544195633-Acetonyl-2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

生成物 1

HCID 537724793-Acetonyl-2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-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 85% pure m-chloroperbenzoic acid (1.6 g) in methylene chloride (50 cc) is added, in the course of 20 minutes, to a solution, cooled to 0° C., of a mixture of the 3-acetonyl-2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene and -oct-3-ene isomers (6.7 g) in methylene chloride (100 cc). The mixture is stirred for 11/2 hours at 0° C. and a saturated solution of sodium bicarbonate (50 cc) is then added. The organic phase is decanted, 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 (0.06-0.20) (75 g) (diameter of the column: 3 cm; height: 21 cm). Elution is carried out with a 70/30 (by volumne) ethyl acetate/cyclohexane mixture (1.5 liters), 100 cc fractions being collected. Fractions 7 to 10 are concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C. This yields the syn isomer of 3-acetonyl-2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide (5 g) in the form of a hard yellow foam.

後処理

  1. customThe organic phase is decanted
  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 (0.06-0.20) (75 g) (diameter of the column
  5. washElution
  6. custombeing collected
  7. concentrationFractions 7 to 10 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-5c7c2f13c0684f86ad49e409817075c9
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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