Cesium carbonate → methyl 4-(5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}-2-fluorophenoxy)-2,2-dimethylbutanoate

HRID 1785982

反応式

HRID 1785982 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([F:29])=[C:25]([OH:30])[CH:24]=3)[C@@H:14]([CH3:32])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:40][CH2:41][C:42]([CH3:48])([CH3:47])[C:43]([O:45][CH3:46])=[O:44]>CN(C=O)C>[C:9]([N:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C@H:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([C:22]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([CH:24]=2)[O:30][CH2:40][CH2:41][C:42]([CH3:48])([CH3:47])[C:43]([O:45][CH3:46])=[O:44])=[O:31])[C@@H:14]([CH3:32])[CH2:13]1)(=[O:11])[CH3:10]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 14928877Butanoic acid, 4-bromo-2,2-dimethyl-, methyl esterHCID 57595472N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-fluoro-3-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide

生成物 1

HCID 57595420methyl 4-(5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}-2-fluorophenoxy)-2,2-dimethylbutanoate収率 52%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-fluoro-3-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (476 mg, 1.05 mmol) was dissolved in DMF at room temperature and Cs2CO3 (854 mg, 2.63 mmol) was added. Methyl 4-bromo-2,2-dimethylbutanoate (702 mg, 1.58 mmol) was added and the reaction was stirred at r.t. overnight. The reaction mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water, then extracted three times with ethyl acetate, dried over MgSO4, filtered and concentrated down. The crude residue was purified by silica gel chromatography (hexanes-ethyl acetate system) to afford methyl 4-(5-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}-2-fluorophenoxy)-2,2-dimethylbutanoate (286 mg, 52%).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated down
  7. customThe crude residue was purified by silica gel chromatography (hexanes-ethyl acetate system)

出典と根拠

ORDレコード
ord-fc90f4123de642d0ab9537c5d7803333
出典データセット
uspto-grants-2009_03
特許番号
US07504508B2

関連ノート

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