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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
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HRID 720885 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-14a6c6a026854fbd8eef985dd6f0b81a
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07135483B2

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