Azacyclonol → Methyl 2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoate hydrochloride

HRID 411919노트

반응식

HRID 411919 반응식
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:19])([CH3:18])[C:14]([O:16][CH3:17])=[O:15])=[CH:9][CH:8]=1)=[O:6].[C:20]1([C:26]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[OH:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[ClH:1].[OH:27][C:26]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH:28]1[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([CH3:19])([CH3:18])[C:14]([O:16][CH3:17])=[O:15])=[CH:9][CH:8]=2)=[O:6])[CH2:30][CH2:29]1

참가 물질

4

반응물 2

HCID 15723AzacyclonolHCID 10062338Methyl 4-(4-chloro-1-oxobutyl)-alpha,alpha-dimethylbenzeneacetate

생성물 1

HCID 22471930Methyl 2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoate hydrochloride수율 76.3%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Dissolve 2-[4-(4-chloro-butyryl)-phenyl]-2-methyl-propionic acid, methyl ester (2.82 g, 10.0 mmol) and α,α-diphenyl-4-piperidinemethanol (5.58 g, 21.0 mmol) in toluene (20 mL). Reflux for 29 hours, cool in an ice bath, filter, filter the filtrate though silica gel (5 g) and wash the gel with toluene (10 mL). Evaporate the solvent in vacuo and dissolve the residue in ethyl ether (100 mL). Add anhydrous hydrogen chloride and filter to give the title compound as an off-white powder (4.2 g, 76%); mp 165-175° C.

후처리

  1. temperatureReflux for 29 hours
  2. temperaturecool in an ice bath
  3. filtrationfilter
  4. filtrationfilter the filtrate though silica gel (5 g)
  5. washwash the gel with toluene (10 mL)
  6. customEvaporate the solvent in vacuo
  7. dissolutiondissolve the residue in ethyl ether (100 mL)
  8. filtrationAdd anhydrous hydrogen chloride and filter

출처 및 근거

ORD 기록
ord-5b828f2ebb914fa48eccb0905a8950f1
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559312B2

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