Trifluoroacetic acid → HCID 69458136, 화합물

HRID 1351949노트

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HRID 1351949 반응식
[CH2:1]([N:3]([CH2:43][CH3:44])[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[C:11]2[CH2:15][C@H:16]([N:18]([CH2:26][C@H:27]([OH:42])[C:28]1[CH:29]=[CH:30][C:31]2[O:36][CH2:35][CH2:34][N:33]([S:37]([CH3:40])(=[O:39])=[O:38])[C:32]=2[CH:41]=1)C(=O)OC(C)(C)C)[CH3:17])=[O:5])[CH3:2].[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48].C1(SC)C=CC=CC=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48].[CH2:43]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[C:11]2[CH2:15][C@H:16]([NH:18][CH2:26][C@H:27]([OH:42])[C:28]1[CH:29]=[CH:30][C:31]2[O:36][CH2:35][CH2:34][N:33]([S:37]([CH3:40])(=[O:39])=[O:38])[C:32]=2[CH:41]=1)[CH3:17])=[O:5])[CH3:44]

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acid3회HCID 7520ThioanisoleHCID 516892Sodium BicarbonateHCID 86760490HCID 86760490, 화합물

생성물 1

HCID 69458136HCID 69458136, 화합물수율 13%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl [2-(7-diethylcarbamoyl-1H-indol-3-yl)-(1R)-1-methylethyl]-[(2R)-2-hydroxy-2-(4-methanesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)ethyl]carbamate (48.4 mg, 0.077 mmol) in methylene chloride (3 mL) is added trifluoroacetic acid (250 μL) under nitrogen atmosphere, and the mixture is stirred at room temperature for 18 hours, and to the mixture is added trifluoroacetic acid (1 mL). The mixture is stirred at room temperature for 3 hours, and thereto are added trifluoroacetic acid (1 mL) and thioanisole (50 μL). The mixture is stirred at room temperature for one hour. The pH value of the reaction solution is adjusted to pH 8 with a saturated aqueous sodium hydrogen carbonate solution, and the solvent is distilled off. The residue is dissolved in chloroform:methanol (2:1, 75 mL), and the insoluble materials are removed by filtration. The solvent is removed by distillation, and the crude product is purified by preparative TLC (a saturated ammonia solution in chloroform) and prepartive HPLC (trifluoroacetic acid-acetonitrile-water) to give the desired 3-{(2R)-2-[(2R)-2-hydroxy-2-(4-methanesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)ethylamino]propyl}-1H-indole-7-carboxylic acid diethylamide trifluoroacetate (6.6 mg, 0.0103 mmol, yield: 13%).

후처리

  1. stirringThe mixture is stirred at room temperature for 3 hours
  2. stirringThe mixture is stirred at room temperature for one hour
  3. distillationthe solvent is distilled off
  4. dissolutionThe residue is dissolved in chloroform:methanol (2:1, 75 mL)
  5. customthe insoluble materials are removed by filtration
  6. customThe solvent is removed by distillation
  7. customthe crude product is purified by preparative TLC (a saturated ammonia solution in chloroform) and prepartive HPLC (trifluoroacetic acid-acetonitrile-water)

출처 및 근거

ORD 기록
ord-b044f61d3e6c400d9aa2d1503dcf69a6
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217724B2

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