Dimethyl Sulfoxide → HCID 19966094, 화합물

HRID 1734863노트

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HRID 1734863 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH:23]([OH:31])[CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:17][C:16]=1[NH:32][C:33](=[O:49])[CH2:34][CH:35]1[C:48]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[O:42][C:41]2[C:36]1=[CH:37][CH:38]=[CH:39][CH:40]=2)([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(OCC)C.C(Cl)Cl>[C:11]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23](=[O:31])[CH2:24][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)=[CH:17][C:16]=1[NH:32][C:33](=[O:49])[CH2:34][CH:35]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:41]=2[O:42][C:43]2[C:48]1=[CH:47][CH:46]=[CH:45][CH:44]=2)([CH3:14])([CH3:12])[CH3:13]

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19966195HCID 19966195, 화합물

생성물 1

HCID 19966094HCID 19966094, 화합물수율 91%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매4회

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온도
-78 °C

실험 절차

1 ml of a methylene chloride solution containing 16 mg (0.13 mmol) of oxalyl chloride was cooled to -78° C. 1.5 ml of a methylene chloride solution containing 20 mg (0.25 mmol) of dimethyl sulfoxide were then added to this solution. The resulting mixture was then stirred for 5 minutes, after which 1 ml of a methylene chloride solution containing 56 mg (0.11 mmol) of N-[2-t-butyl-5-(4-cyclohexyl-3-hydroxybutyl)phenyl]-2-(9H-xanthen-9-yl)acetamide (prepared as described in Example 12) was added dropwise over a period of 5 minutes at the same temperature. The mixture was then stirred for 15 minutes, and then 1 ml of a methylene chloride solution containing 64 mg (0.64 mmol) of triethylamine was added dropwise to it. The mixture was stirred for 10 minutes, and then the reaction mixture was allowed to return to room temperature. The reaction solution was diluted with diethyl ether, and washed with dilute aqueous hydrochloric acid and then with water. The solvent was then removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 10 g of silica gel. Elution with a 100:8 by volume mixture of methylene chloride and ethyl acetate afforded 51 mg (yield 91%) of the title compound as crystals, melting at 154°-155° C. (after recrystallization from a mixture of diethyl ether and hexane).

후처리

  1. additionwere then added to this solution
  2. additionwas added dropwise over a period of 5 minutes at the same temperature
  3. stirringThe mixture was then stirred for 15 minutes
  4. additionwas added dropwise to it
  5. stirringThe mixture was stirred for 10 minutes
  6. customto return to room temperature
  7. washwashed with dilute aqueous hydrochloric acid
  8. customThe solvent was then removed by distillation under reduced pressure
  9. washElution with a 100:8
  10. additionby volume mixture of methylene chloride and ethyl acetate

출처 및 근거

ORD 기록
ord-7e123675b8d346d0b8f7e92e5b258947
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05534529

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