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

HRID 2243544ノート

反応式

HRID 2243544 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f3e3a25249594cf3a8bcc029c2e99982
出典データセット
uspto-grants-2010_03
特許番号
US07674938B2

反応ノート

読み込み中…