Dimethyl Sulfoxide → HCID 178474986、化合物

HRID 1961657ノート

反応式

HRID 1961657 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([NH:20][C:21](=[O:23])[CH3:22])[CH2:16][CH2:15]1.CCN(CC)CC>C(Cl)Cl.O.C(Cl)Cl.CO>[O:11]=[CH:12][CH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([NH:20][C:21](=[O:23])[CH3:22])[CH2:16][CH2:15]1

参加物

8

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178474987HCID 178474987、化合物

生成物 1

HCID 178474986HCID 178474986、化合物収率 81%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回HCID 21226129Dichloromethane methanol溶媒

実験手順

DMSO (3.68 g, 47 mmol) in CH2Cl2 (20 ml) was added at −78° C. to a stirred solution of oxalylchloride (2.9 g, 23 mmol) in CH2Cl2 (100 ml). After 1 h stirring at −78° C. a solution of N-[trans-4-(2-hydroxy-ethyl)-cyclohexyl]-acetamide (2.18 g, 12 mmol) in CH2Cl2 (80 ml) was added followed after 2 h by Et3N (7.14 g, 71 mmol). The mixture was allowed to reach room temperature and was then diluted with H2O and extracted with CH2Cl2. The combined organic layers were dryed (Na2SO4) and the solvent was evaporated to afford the crude product. Chromatography (CH2Cl2/MeOH 95:5) yielded 1.75 g (81%, 9.5 mmol) of a light brown solid. MS (m/z): 184.3 ([M+H])+.

後処理

  1. additionwas added
  2. customto reach room temperature
  3. extractionextracted with CH2Cl2
  4. customthe solvent was evaporated
  5. customto afford the crude product

出典と根拠

ORDレコード
ord-a56a9a59839c44dc808e5d145256596b
出典データセット
uspto-grants-2013_04
特許番号
US08415350B2

反応ノート

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