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

HRID 1044565ノート

反応式

HRID 1044565 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ff93ef626cb94b83a0d9ee897ea623a1
出典データセット
uspto-grants-2013_10
特許番号
US08563582B2

反応ノート

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