Water → 3-{3-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-propionic acid methyl ester

HRID 2103437ノート

反応式

HRID 2103437 の反応式
[CH2:1]([C:5]1[N:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[S:8][C:9]=1[CH2:10]Cl)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].[OH:28][C:29]1[CH:30]=[C:31]([CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])[CH:32]=[CH:33][CH:34]=1.O>CN(C=O)C>[CH3:40][O:39][C:37](=[O:38])[CH2:36][CH2:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([O:28][CH2:10][C:9]2[S:8][C:7]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)=[N:6][C:5]=2[CH2:1][CH2:2][CH2:3][CH3:4])[CH:30]=1

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 1512675Methyl 3-(3-hydroxyphenyl)propionateHCID 230893954-Butyl-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole

生成物 1

HCID 578043033-{3-[4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-propionic acid methyl ester収率 67.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-butyl-5-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole (300 mg, 0.90 mmol) in anhydrous DMF (5 mL) add cesium carbonate (586 mg, 1.80 mmol) and methyl 3-(3-hydroxyphenyl)propionate (178 mg, 0.99 mmol). Stir the resulting mixture overnight then pour into water and extract twice with ethyl acetate. Wash the combined extracts with water, dry over MgSO4, filter and concentrate under vacuum. Purify the residue by flash chromatography on silica gel (eluting with 5% ethyl acetate in heptane) to give the title compound (290 mg) as a yellow oil.

後処理

  1. extractionextract twice with ethyl acetate
  2. washWash the combined extracts with water
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate under vacuum
  6. customPurify the residue by flash chromatography on silica gel (eluting with 5% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-7c378f3cbbb14ffda35a60b676e91876
出典データセット
uspto-grants-2009_08
特許番号
US07576109B2

反応ノート

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