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Dimethyl Sulfoxide → HCID 67065856, 화합물

HRID 604339
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HRID 604339 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([N:30]1[CH2:34][CH2:33][C@@H:32]([OH:35])[CH2:31]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[C:11]([N:30]1[CH2:34][CH2:33][C:32](=[O:35])[CH2:31]1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 58455161HCID 58455161, 화합물

생성물 1

HCID 67065856HCID 67065856, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

반응 조건

온도
-60 °C

실험 절차

To a stirred solution of anhydrous dichloromethane (35.0 mL) in a 3-necked flask with a thermometer, oxalyl chloride (1.5 mL) was added and the resulting solution was cooled to −60° C. A solution of dimethylsulfoxide (2.6 mL) in dichloromethane (7.5 mL) was added over a period of 10 min, and then (3R)-1-tritylpyrrolidin-3-ol (5.0 g) in dichloromethane (15.0 mL) was added over a period of 10 min. The resulting solution was stirred at −60° C. for 15 min, then triethylamine (10.6 mL) was added over a period of 5 min. After 5 min, the cooling bath was removed and the mixture was allowed to warm to room temperature. Water (45 mL) was added. The mixture was stirred for an additional 30 min and then extracted with dichloromethane. The organic phase was washed with 5% aqueous citric acid solution, dried over anhydrous sodium sulfate, filtered and concentrated to yield the title compound. LC-MS=243.1 (M+1).

후처리

  1. waitAfter 5 min
  2. customthe cooling bath was removed
  3. temperatureto warm to room temperature
  4. additionWater (45 mL) was added
  5. stirringThe mixture was stirred for an additional 30 min
  6. extractionextracted with dichloromethane
  7. washThe organic phase was washed with 5% aqueous citric acid solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e36450ee9c404cef81211f4b6bc6f4e2
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07910596B2

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