Triphenylphosphine → 3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-benzoic acid methyl ester hydrochloride salt

HRID 229115ノート

反応式

HRID 229115 の反応式
[Cl:1][C:2]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]([CH2:10][CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][CH2:7][CH2:8][OH:9].[CH3:32][O:33][C:34](=[O:42])[C:35]1[CH:40]=[CH:39][CH:38]=[C:37](O)[CH:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[ClH:1].[CH3:32][O:33][C:34](=[O:42])[C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([O:9][CH2:8][CH2:7][CH2:6][N:5]([CH2:4][C:3]2[CH:24]=[CH:25][CH:26]=[C:27]([C:28]([F:29])([F:30])[F:31])[C:2]=2[Cl:1])[CH2:10][CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:36]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 88068Methyl 3-HydroxybenzoateHCID 5363146Diisopropyl azodicarboxylateHCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-ol

生成物 1

HCID 688654923-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-benzoic acid methyl ester hydrochloride salt収率 60.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 3-[(2-chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propan-1-ol (0.60 g, 1.34 mmol) in toluene (4 mL) at RT was added 3-hydroxy-benzoic acid methyl ester (0.22 g, 1.45 mmol). The mixture was treated with polymer bound triphenylphosphine (0.82 g, 2.50 mmol, 3 mmol/g, Fluka Chemie) (0.71 g, 2.14 mmol, 3 mmol/g, Fluka Chemie). After 15 minutes of stirring, the mixture was treated with DIAD (0.33 mL, 1.67 mmol) and was stirred overnight at RT. The reaction mixture was filtered, concentrated and 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 (0.25 g, 32%); MS (ES+) m/e 583 [M+H]+.

後処理

  1. additionThe mixture was treated with polymer
  2. stirringwas stirred overnight at RT
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. custompurified 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-79c78efefef843af88d2ffd62ceb66a8
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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