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Glycine methyl ester → [2-(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-ethylamino]-acetic Acid Methyl Ester

HRID 902695
ノート
印刷プレビュー

反応式

HRID 902695 の反応式
[Cl:1][C:2]1[C:36]([C:37]([F:40])([F:39])[F:38])=[CH:35][CH:34]=[CH:33][C:3]=1[CH2:4][N:5]([CH2:19][CH:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH2:16][CH:17]=O)[CH:13]=[CH:14][CH:15]=1.[CH3:41][O:42][C:43](=[O:46])[CH2:44][NH2:45].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C>[CH3:41][O:42][C:43](=[O:46])[CH2:44][NH:45][CH2:17][CH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH2:8][CH2:7][CH2:6][N:5]([CH2:4][C:3]2[CH:33]=[CH:34][CH:35]=[C:36]([C:37]([F:38])([F:40])[F:39])[C:2]=2[Cl:1])[CH2:19][CH:20]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 69221Glycine methyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 86598296(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-acetaldehyde

生成物 1

HCID 69251469[2-(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-ethylamino]-acetic Acid Methyl Ester

試薬・触媒・溶媒 2

HCID 176
Acetic Acid
触媒
HCID 111,2-Dichloroethane溶媒

実験手順

To a solution of (3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-acetaldehyde (76 mg, 0.13 mmol) and glycine methyl ester (34 mg, 0.27 mmol) in 1,2-dichloroethane (15 ml) was stirred as room temperature for 10 minutes, and sodium triacetoxyborohydride (57 mg, 0.27 mmol) was added. Next two drops of glacial acetic acid was added. The reaction mixture was stirred at room temperature for 18 hour and then quenched with 0.01N aqueous HCl (15 ml) The biphasic mixture was separated and the aqueous layer was extracted with dichloromethane (3×). The organic layers were combined with the 1,2-dichloroethane solution and were washed with brine (1×), dried over sodium sulphate, filtered and concentrated in vacuo. Preparative HPLC (YMC 75×30 mm, 25 ml/min, 90-100% CH3CN) afforded title compound as an oil, 70 mg (81%).

後処理

  1. customquenched with 0.01N aqueous HCl (15 ml) The biphasic mixture
  2. customwas separated
  3. extractionthe aqueous layer was extracted with dichloromethane (3×)
  4. washwere washed with brine (1×)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2c4b2760b61945e8b91a6fe7a7bcea6f
出典データセット
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07365085B2

反応ノート

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