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Dimethyl Sulfoxide → 1,1,1-Trifluoro-3-[(N-acetylprolyl)alanylprolylamino]-butane-2,2-diol

HRID 1440058
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HRID 1440058 반응식
C(Cl)(=O)C(Cl)=[O:3].CS(C)=O.[F:11][C:12]([F:41])([F:40])[CH:13]([OH:39])[CH:14]([NH:16][C:17](=[O:38])[C@@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[C:23](=[O:37])[C@H:24]([CH3:36])[NH:25][C:26](=[O:35])[C@@H:27]1[CH2:31][CH2:30][CH2:29][N:28]1[C:32](=[O:34])[CH3:33])[CH3:15].C(N(CC)CC)C>C(Cl)Cl>[F:41][C:12]([F:11])([F:40])[C:13]([OH:3])([OH:39])[CH:14]([NH:16][C:17](=[O:38])[C@@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[C:23](=[O:37])[C@H:24]([CH3:36])[NH:25][C:26](=[O:35])[C@@H:27]1[CH2:31][CH2:30][CH2:29][N:28]1[C:32](=[O:34])[CH3:33])[CH3:15]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 145032661,1,1-Trifluoro-3-[(N-acetylprolyl)alanylprolylamino]butan-2-ol

생성물 1

HCID 537705141,1,1-Trifluoro-3-[(N-acetylprolyl)alanylprolylamino]-butane-2,2-diol

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

To a solution of oxalyl chloride (72 μl, 0.83 mmol) in methylene chloride (1 ml) under an argon atmosphere and cooled in a dry ice-acetone bath was added dimethylsulfoxide (0.12 ml, 1.65 mmol) with stirring. After 5 minutes, a solution of the compound of example 57 (0.25 g, 0.55 mmol) in methylene chloride (1.5 ml) was added. The reaction mixture was stirred for 15 minutes, triethylamine (0.50 ml,3.58 mmol) then added and the reaction warmed to room temperature for 30 minutes. The reaction mixture was placed directly onto a silica gel column and eluted with methylene chloride-methanol. Trituration of the resultant oily solid with ether-hexane and filtration gave the above-named product, (50 mg, 0.11 mmol).

후처리

  1. stirringThe reaction mixture was stirred for 15 minutes
  2. washeluted with methylene chloride-methanol
  3. filtrationTrituration of the resultant oily solid with ether-hexane and filtration
  4. customgave the above-named product, (50 mg, 0.11 mmol)

출처 및 근거

ORD 기록
ord-3fc4580e47354547a6e29c730d7ec59e
출처 데이터셋
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05496927

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