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

HRID 1436765노트

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HRID 1436765 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>[CH:36]([C@:30]1([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])[CH2:31][CH2:32][C@@H:28]([NH:27][C:25](=[O:26])[O:24][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:29]1)([CH3:38])[CH3:37]

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%EtOAclhexanes) 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%EtOAclhexanes)

출처 및 근거

ORD 기록
ord-bb5b1382aa194180b2f48b7dc9becc05
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618970B2

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