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Dimethyl Sulfoxide → HCID 131722001、化合物

HRID 1954031
ノート
印刷プレビュー

反応式

HRID 1954031 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][CH2:12][C@H:13]1[C:43](=[O:44])[CH2:42][C@H:41]([OH:45])[C@@H:40]([CH3:46])[C@@H:39](/[C:47](/[CH3:58])=[CH:48]/[C@H:49]2[CH2:54][C@@H:53]([O:55][CH3:56])[C@H:52]([OH:57])[CH2:51][CH2:50]2)[O:38][C:36](=[O:37])[C@H:35]2[N:30]([CH2:31][CH2:32][CH2:33][CH2:34]2)[C:28](=[O:29])[C:26](=[O:27])[C@:24]2([OH:59])[O:25][C@@H:20]([C@@H:21]([O:61][CH3:62])[CH2:22][C@H:23]2[CH3:60])[C@@H:19]([O:63][CH3:64])[CH2:18][C@@H:17]([CH3:65])[CH2:16][C:15]([CH3:66])=[CH:14]1.C(N(CC)CC)C>C(Cl)Cl.CCOCC>[CH2:12]([C@@H:13]1[CH:14]=[C:15]([CH3:66])[CH2:16][C@H:17]([CH3:65])[CH2:18][C@H:19]([O:63][CH3:64])[C@H:20]2[O:25][C@:24]([OH:59])([C@H:23]([CH3:60])[CH2:22][C@@H:21]2[O:61][CH3:62])[C:26](=[O:27])[C:28](=[O:29])[N:30]2[C@@H:35]([CH2:34][CH2:33][CH2:32][CH2:31]2)[C:36](=[O:37])[O:38][C@H:39](/[C:47](/[CH3:58])=[CH:48]/[C@@H:49]2[CH2:50][CH2:51][C:52](=[O:57])[C@H:53]([O:55][CH3:56])[CH2:54]2)[C@H:40]([CH3:46])[C@@H:41]([OH:45])[CH2:42][C:43]1=[O:44])[CH3:11]
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

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 5282071Ascomycin

生成物 1

HCID 131722001HCID 131722001、化合物収率 59.5%

試薬・触媒・溶媒 2

HCID 3283
Diethyl Ether
溶媒
HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-70 °C

実験手順

Methylsulfide-chlorine complex was prepared by adding oxalyl chloride (0.32 g) into a solution of dimethylsulfoxide (0.44 g) in 4 mL of methylene chloride and stirred at -70° C. for 30 minutes. The solution of the complex was slowly added to a stirred solution of ascomycin (1.6 g) in 5 mL of methylene chloride at -70° C. After stirring for 30 minutes, triethylamine (1.4 g) was added and the mixture was allowed to stir for an additional 30 minutes at -70° C. The reaction mixture was then allowed to warm to room temperature followed by additional stirring for 1 hour. The reaction mixture was diluted with 100 mL of ether, washed with 1N-HCl aq. solution (30 mL×2), brine (30 mL), dried over magnesium sulfate anhydrous, and the solvent removed in vacuo. The crude product was purified on 70 gram of silica gel, eluting with ether to obtain 0.95 g of the title compound.

後処理

  1. customMethylsulfide-chlorine complex was prepared
  2. stirringAfter stirring for 30 minutes
  3. stirringto stir for an additional 30 minutes at -70° C
  4. temperatureto warm to room temperature
  5. stirringby additional stirring for 1 hour
  6. washwashed with 1N-HCl aq. solution (30 mL×2), brine (30 mL)
  7. dry with materialdried over magnesium sulfate anhydrous
  8. customthe solvent removed in vacuo
  9. customThe crude product was purified on 70 gram of silica gel
  10. washeluting with ether

出典と根拠

ORDレコード
ord-6848ebff6d534c9fb21533654e1fa263
出典データセット
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06121257

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート