Water → benzyl 4'-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethylamino]ethoxy)-3',5'-dimethylbiphenyl-4-carboxylate

HRID 2243544노트

반응식

HRID 2243544 반응식
CS(O[CH2:6][CH2:7][O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])=[CH:18][CH:17]=2)=[CH:11][C:10]=1[CH3:32])(=O)=O.[NH2:33][C@@H:34]([CH3:44])[C@@H:35]([C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1)[OH:36].C(NC(C)C)(C)C.O>CN(C)C=O.C(OCC)(=O)C>[OH:36][C@H:35]([C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=1)[C@@H:34]([NH:33][CH2:6][CH2:7][O:8][C:9]1[C:10]([CH3:32])=[CH:11][C:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:23])=[CH:18][CH:17]=2)=[CH:13][C:14]=1[CH3:15])[CH3:44]

참가 물질

7

반응물 4

HCID 962WaterHCID 7912DiisopropylamineHCID 6931143P-HydroxynorephedrineHCID 23090786Benzyl 4'-(2-methanesulfonyloxy-ethoxy)-3'5'-dimethylbiphenyl-4-carboxylate

생성물 1

HCID 68544588benzyl 4'-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethylamino]ethoxy)-3',5'-dimethylbiphenyl-4-carboxylate수율 46.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

A mixture of benzyl 4′-(2-methanesulfonyloxyethoxy)-3′, 5′-dimethylbiphenyl-4-carboxylate (0.20 g), 4-((1R,2S)-2-amino-1-hydroxypropyl)phenol (0.074 g) and diisopropylamine (0.074 mL) in N,N-dimethylformamide (2 mL) was stirred at 80° C. overnight. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: methylene chloride/methanol=15/1-10/1) to afford benzyl 4′-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethylamino]ethoxy}-3′,5′-dimethylbiphenyl-4-carboxylate (0.108 g).

후처리

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: methylene chloride/methanol=15/1-10/1)

출처 및 근거

ORD 기록
ord-f3e3a25249594cf3a8bcc029c2e99982
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674938B2

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