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Acetic Acid → 3-(2-Methyl-4-{[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenyl)-propionic acid methyl ester

HRID 854567
ノート
印刷プレビュー

反応式

HRID 854567 の反応式
[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[CH3:13].[CH3:15][C:16]1[N:17]=[C:18]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)[S:19][C:20]=1[CH:21]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:21][C:20]2[S:19][C:18]([C:23]3[CH:24]=[CH:25][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:27][CH:28]=3)=[N:17][C:16]=2[CH3:15])=[CH:8][C:7]=1[CH3:13]
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 4

HCID 176Acetic AcidHCID 27828994-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 54187007Methyl 3-(4-amino-2-methylphenyl)propanoate

生成物 1

HCID 694694953-(2-Methyl-4-{[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethyl]-amino}-phenyl)-propionic acid methyl ester収率 68%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-(4-Amino-2-methyl-phenyl)-propionic acid methyl ester (0.14 g, 0.70 mmol) and 4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbaldehyde (0.19 g, 0.71 mmol) in anhydrous CH2Cl2 (5 mL) is added 4 Å molecular sieves followed by acetic acid (50 μL, 0.87 mmol). The mixture is stirred at RT for 2 h. Sodium triacetoxyborohydride (0.22 g, 1.04 mmol) is added, and the mixture is stirred at RT for 12 h. The reaction is quenched with saturated NaHCO3. The organics are separated and washed with saturated NaHCO3 and brine, and dried with MgSO4. The crude material is purified by flash chromatography to yield the title compound (0.21 g, 68%).

後処理

  1. stirringthe mixture is stirred at RT for 12 h
  2. customThe reaction is quenched with saturated NaHCO3
  3. customThe organics are separated
  4. washwashed with saturated NaHCO3 and brine
  5. dry with materialdried with MgSO4
  6. customThe crude material is purified by flash chromatography

出典と根拠

ORDレコード
ord-71d28ee2a87848cabf662a76b08a4fda
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07259175B2

反応ノート

読み込み中…

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