Lithium hydroxide, monohydrate → N-(2,2-Diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-(3-carboxyphenoxy)propylamine, hydrochloride

HRID 229116ノート

反応式

HRID 229116 の反応式
C[O:2][C:3](=[O:41])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[C:31]=2[Cl:40])[CH2:15][CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=1.O[Li].O>C1COCC1.O>[ClH:40].[Cl:40][C:31]1[C:32]([C:36]([F:37])([F:38])[F:39])=[CH:33][CH:34]=[CH:35][C:30]=1[CH2:29][N:14]([CH2:15][CH:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:13][CH2:12][CH2:11][O:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:41])=[O:2]

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrate2 回HCID 577571333-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-benzoic acid methyl ester

生成物 1

HCID 68861721N-(2,2-Diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-(3-carboxyphenoxy)propylamine, hydrochloride収率 134.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-benzoic acid methyl ester (0.200 g, 0.344 mmol) in THF (7.5 mL) and H2O (2.5 mL) at RT LiOH.H2O (0.029 g, 0.688 mmol) was added. The mixture was stirred overnight at RT. The mixture was then treated with more LiOH.H2O (0.058 g, 1.376 mmol) and heated at 50° C. overnight. The completed reaction was cooled to 0° C. and was quenched with a minimal amount of H2O. The mixture was the acidified to a pH=2 with concentrated HCl. The mixture was then extracted three times with EtOAc and was dried, filtered and concentrated to afford a foam that was purified via preparative HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile:H2O, UV detection at 254 nm) to yield the title compound (0.14 g, 72%); MS (ES+) m/e 569 [M+H]+.

後処理

  1. temperatureheated at 50° C. overnight
  2. customThe completed reaction
  3. temperaturewas cooled to 0° C.
  4. customwas quenched with a minimal amount of H2O
  5. extractionThe mixture was then extracted three times with EtOAc
  6. customwas dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a foam that
  10. customwas purified via preparative HPLC (TMC CombiPrep PDS, 75×30 mm, 25 mL/min, acetonitrile:H2O, UV detection at 254 nm)

出典と根拠

ORDレコード
ord-fb01fd29e94d429683011d265cff3a60
出典データセット
uspto-grants-2009_07
特許番号
US07560586B2

反応ノート

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