Triethylamine → tert-Butyl [(1R,3S)-3-Isopropyl-3-({4-[5-(trifluoromethyl)pyridin-3-yl]piperazin-1-yl}carbonyl)cyclopentyl]carbamate

HRID 1044565노트

반응식

HRID 1044565 반응식
Cl.Cl.Cl.[F:4][C:5]([F:19])([F:18])[C:6]1[CH:7]=[C:8]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:9]=[N:10][CH:11]=1.[C:20]([O:24][C:25]([NH:27][C@@H:28]1[CH2:32][CH2:31][C@:30]([CH:36]([CH3:38])[CH3:37])([C:33](O)=[O:34])[CH2:29]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl.CCOC(C)=O>[C:20]([O:24][C:25](=[O:26])[NH:27][C@@H:28]1[CH2:32][CH2:31][C@:30]([CH:36]([CH3:37])[CH3:38])([C:33]([N:15]2[CH2:16][CH2:17][N:12]([C:8]3[CH:9]=[N:10][CH:11]=[C:6]([C:5]([F:18])([F:4])[F:19])[CH:7]=3)[CH2:13][CH2:14]2)=[O:34])[CH2:29]1)([CH3:23])([CH3:22])[CH3:21]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 60122293(1S,3R)-3-((Tert-butoxycarbonyl)amino)-1-isopropylcyclopentanecarboxylic acidHCID 866415371-[5-(Trifluoromethyl)pyridin-3-yl]piperazine trihydrochloride

생성물 1

HCID 59833540tert-Butyl [(1R,3S)-3-Isopropyl-3-({4-[5-(trifluoromethyl)pyridin-3-yl]piperazin-1-yl}carbonyl)cyclopentyl]carbamate수율 170.5%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-[5-(trifluoromethyl)pyridin-3-yl]piperazine trihydrochloride (0.22 g, 0.23 mmol), (1S,3R)-3-[(tert-butoxycarbonyl)amino]-1-isopropylcyclopentanecarboxylic acid (0.18 g, 0.66 mmol) in methylene chloride (10 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.338 g, 0.764 mmol) followed by triethylamine (0.22 mL, 1.6 mmol). The mixture was stirred at room temperature overnight and diluted with EtOAc. The solution was washed with saturated NaHCO3, dried (MgSO4) and concentrated. The residue was purified by flash chromatography on silica gel (20% EtOAc/hexanes to 40% EtOAc/hexanes) to give 0.19 g (61%) of desired product. MS calculated for C24H35F3N4O3: (M+H) 485; found 485.2.

후처리

  1. washThe solution was washed with saturated NaHCO3
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel (20% EtOAc/hexanes to 40% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-ff93ef626cb94b83a0d9ee897ea623a1
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563582B2

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