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

HRID 720885
ノート
印刷プレビュー

反応式

HRID 720885 の反応式
C(OC(=O)[NH:7][CH:8]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH:9]([OH:39])[CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17](=[O:38])[NH:18][CH:19]([CH2:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:12]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:32]1([CH2:31][CH2:30][CH2:29][CH:19]([NH:18][C:17]([CH:13]2[CH2:14][CH2:15][CH2:16][N:11]([CH2:10][CH:9]([OH:39])[CH:8]([NH2:7])[CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:12]2)=[O:38])[CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 18727510(1-Benzyl-2-hydroxy-3-{3-[4-phenyl-1-(3-phenyl-propyl)-butylcarbamoyl]-piperidine-1-yl}-propyl)-carbamic acid tert-butyl ester

生成物 1

HCID 187274631-(3-Amino-2-hydroxy-4-phenyl-butyl)-piperidine-3-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide収率 92.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(1-Benzyl-2-hydroxy-3-{3-[4-phenyl-1-(3-phenyl-propyl)-butylcarbamoyl]-piperidine-1-yl}-propyl)-carbamic acid tert-butyl ester (19) (194.4 mg; 0.3 mmol) is dissolved in methylene chloride (5 mL) at ambient temperature. Trifluoroacetic acid (5 mL) is added in a slow stream, and the solution is stirred for 90 minutes at ambient temperature. The solution is concentrated in vacuo at 40° C. The residue is slurried in a mixture of methylene chloride (10 mL) and water (100 mL), then potassium carbonate is added until the slurry is alkaline. The slurry is diluted with water (50 mL) then extracted with methylene chloride (3×50 mL). The organic extracts are dried over MgSO4, filtered, and concentrated in vacuo affording the desired product (150 mg) as an oil.

後処理

  1. concentrationThe solution is concentrated in vacuo at 40° C
  2. additionThe residue is slurried in a mixture of methylene chloride (10 mL) and water (100 mL)
  3. additionpotassium carbonate is added until the slurry
  4. additionThe slurry is diluted with water (50 mL)
  5. extractionthen extracted with methylene chloride (3×50 mL)
  6. dry with materialThe organic extracts are dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-14a6c6a026854fbd8eef985dd6f0b81a
出典データセット
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07135483B2

反応ノート

読み込み中…

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