Dimethyl Sulfoxide → HCID 178474986, 화합물

HRID 1961657노트

반응식

HRID 1961657 반응식
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

참가 물질

8

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178474987HCID 178474987, 화합물

생성물 1

HCID 178474986HCID 178474986, 화합물수율 81%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매3회HCID 21226129Dichloromethane methanol용매

실험 절차

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])+.

후처리

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

출처 및 근거

ORD 기록
ord-a56a9a59839c44dc808e5d145256596b
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415350B2

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