Trifluoroacetic acid → 1-(Piperidine-2-carbonyl)-piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

HRID 393978ノート

反応式

HRID 393978 の反応式
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][N:32]3C(OC(C)(C)C)=O)=[O:30])[CH2:25][CH2:24]2)=[O:22])[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][NH:32]3)=[O:30])[CH2:25][CH2:24]2)=[O:22])[CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 121367451-(1-tert-butoxycarbonylpiperidine-2-carbonyl)-piperidine-4-carboxylic Acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

生成物 1

HCID 121367461-(Piperidine-2-carbonyl)-piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide収率 94%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1-(1-tert-Butoxycarbonylpiperidine-2-carbonyl)-piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (5) (1.41 g; 2.39 mmol) is dissolved in methylene chloride (40 mL) at ambient temperature. Trifluoroacetic acid (20 mL) is added in a slow stream, and the solution is stirred for 1.5 hours at ambient temperature. The solution is concentrated in vacuo at 40° C. The residue is dissolved in methylene chloride (200 mL) and poured onto saturated sodium bicarbonate solution. The pH is adjusted to 9 with saturated potassium carbonate solution. The mixture is shaken the layers separated. The water layer is extracted with methylene chloride (3×50 mL). The combined organic extracts are washed with water, dried over MgSO4, filtered, and concentrated in vacuo affording the desired product (1.10 g) as a white solid. ESMS: MH+ 490.2

後処理

  1. concentrationThe solution is concentrated in vacuo at 40° C
  2. dissolutionThe residue is dissolved in methylene chloride (200 mL)
  3. additionpoured onto saturated sodium bicarbonate solution
  4. stirringThe mixture is shaken the layers
  5. customseparated
  6. extractionThe water layer is extracted with methylene chloride (3×50 mL)
  7. washThe combined organic extracts are washed with water
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a05daa9e636e46eeb9f903e42eec28c6
出典データセット
uspto-grants-2004_10
特許番号
US06809093B2

反応ノート

読み込み中…