Acetic Anhydride → cis-4-[(3,5-Bis-trifluoromethyl-benzyl)-formyl-amino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

HRID 369916ノート

反応式

HRID 369916 の反応式
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:13][CH:14]=2)[C@H:9]([NH:20][CH2:21][C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=2)[CH2:8][C@@H:7]1[CH2:36][CH3:37])=[O:5])[CH3:2].[C:38](OC(=O)C)(=[O:40])C.C([O-])=O.[Na+]>C(O)=O.O>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([F:17])([F:18])[F:19])=[CH:13][CH:14]=2)[C@H:9]([N:20]([CH2:21][C:22]2[CH:27]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:25]=[C:24]([C:32]([F:35])([F:33])[F:34])[CH:23]=2)[CH:38]=[O:40])[CH2:8][C@@H:7]1[CH2:36][CH3:37])=[O:5])[CH3:2]

参加物

6

反応物 3

HCID 7918Acetic AnhydrideHCID 2723810Sodium FormateHCID 86584715cis-4-(3,5-bis-trifluoromethyl-benzylamino)-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

生成物 1

HCID 86755977cis-4-[(3,5-Bis-trifluoromethyl-benzyl)-formyl-amino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester収率 86.4%

試薬・触媒・溶媒 2

HCID 284Formic Acid溶媒HCID 962Water溶媒

実験手順

A solution of cis-4-(3,5-bis-trifluoromethyl-benzylamino)-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (Example 3E) (2.0 g, 3.65 mmol) in 20 mL of formic acid was treated with acetic anhydride (11.29 g, 111 mmol) and sodium formate (1.25 g, 18.5 mmol). After stirring for 24 h at room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated in vacuo to afford the crude product, which was purified by silica gel chromatography using 10-15% ethyl acetate/hexanes as eluent to afford 1.8 g of the title product. MS m/z 571.2 (M+ +1); 1H NMR (~5:1 mixture of formamide rotamers, CDCl3) δ 0.75 (t, 3H), 1.28 (t, 3H), 1.42 (m, 1H), 1.6-1.75 (M, 2H), 2.3 (bm, 1H), 4.15-4.3 (m, 2H), 4.3-4.4 (m, 1H), 4.5-4.7 (bm, 1H), 4.8-5.8 (bm, 2H), 7.14 and 7.08 (s, 1H), 7.5-7.6 (m, 2H), 7.74 (s, 2H), 7.80 and 7.86 (s, 1H), 8.47 and 8.62 (s, 1H).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto afford the crude product, which
  6. customwas purified by silica gel chromatography

出典と根拠

ORDレコード
ord-f73992b3985a4dceb4c8fe86008bdf55
出典データセット
uspto-grants-2000_10
特許番号
US06140343

反応ノート

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