Ethyl Acetate → 2-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-propane-1,3-diol hydrochloride salt

HRID 902629ノート

反応式

HRID 902629 の反応式
C[O:2][C:3](=O)[CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH2:16][CH2:17][N:18]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([F:43])([F:42])[F:41])[C:35]=2[Cl:44])[CH2:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:9]=1)[C:5](O)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>C(OCC)C.[Cl-].[Na+].O>[ClH:44].[Cl:44][C:35]1[C:36]([C:40]([F:41])([F:42])[F:43])=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][N:18]([CH2:19][CH:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:17][CH2:16][CH2:15][O:14][C:10]1[CH:9]=[C:8]([CH:4]([CH2:3][OH:2])[CH2:5][OH:6])[CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 692536562-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-malonic acid monomethyl ester

生成物 1

HCID 692526452-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-propane-1,3-diol hydrochloride salt

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To 2-(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-malonic acid monomethyl ester (22 mg, 0.03 mmol) in diethyl ether (1 ml) was added lithium aluminum hydride (100 uL) at 0° C. The reaction was allowed to warm to room temperature before the addition of brine and ethyl acetate. The combined organic layers were dried over magnesium sulfate and evaporated. The crude product was purified by HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min, A: acetonitrile B: water, A: 60 to 100% during 10 min, UV detection at 254 nm) to give the title compound free amine as an oil. MS m/e 598.2(M+H)+. To a solution of the free amine in diethyl ether was added HCl in diethyl ether (1.0M). The suspension was evaporated and dried to give the title compound as a white solid (2 mg, 10%).

後処理

  1. dry with materialThe combined organic layers were dried over magnesium sulfate
  2. customevaporated
  3. customThe crude product was purified by HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min

出典と根拠

ORDレコード
ord-04e1d3307ccd4df684be57520859a6cb
出典データセット
uspto-grants-2008_04
特許番号
US07365085B2

反応ノート

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