Diisopropylethylamine → HCID 57595487、化合物

HRID 1785987ノート

反応式

HRID 1785987 の反応式
[C:1]([O:4][CH2:5][C:6]([N:8]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C@H:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C@@H:11]([CH3:19])[CH2:10]1)=[O:7])(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[C:37]([C:39]1[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][CH2:47][C:48]([CH3:54])([CH3:53])[C:49]([O:51][CH3:52])=[O:50])=[CH:41][CH:40]=1)=[O:38]>C(Cl)Cl>[C:1]([O:4][CH2:5][C:6]([N:8]([C:20]1[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=1)[C@H:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([C:37]([C:39]2[CH:44]=[CH:43][C:42]([CH2:45][CH2:46][CH2:47][C:48]([CH3:54])([CH3:53])[C:49]([O:51][CH3:52])=[O:50])=[CH:41][CH:40]=2)=[O:38])[C@@H:11]([CH3:19])[CH2:10]1)=[O:7])(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 57421380HCID 57421380、化合物HCID 68921124HCID 68921124、化合物

生成物 1

HCID 57595487HCID 57595487、化合物収率 40%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-{(4-chlorophenyl)[(2S,4R)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}-2-oxoethyl acetate (170 mg, 0.45 mmol, 1 equ.) in methylene chloride (2.0 mL) at room temperature was added diisopropylethylamine (127 uL, 0.73 mmol, 1.60 equ.) followed by methyl 5-[4-(chlorocarbonyl)phenyl]-2,2-dimethylpentanoate (196 mg, 0.73 mmol, 1.60 equ.). The reaction was stirred over night at room temperature. The mixture was concentrated, then poured into water and extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulfate, filtered dried and concentrated. The crude residue was purified by silica gel chromatography (ethyl acetate/hexane 25/75 to 1:1 gradient) to afford the pure methyl 5-(4-{[(2S,4R)-4-[[(acetyloxy)acetyl](4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenyl)-2,2-dimethylpentanoate (110 mg, 40%).

後処理

  1. concentrationThe mixture was concentrated
  2. additionpoured into water
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customdried
  8. concentrationconcentrated
  9. customThe crude residue was purified by silica gel chromatography (ethyl acetate/hexane 25/75 to 1:1 gradient)

出典と根拠

ORDレコード
ord-d66277e98d1f4a59a5cad9023b6c3b9e
出典データセット
uspto-grants-2009_03
特許番号
US07504508B2

反応ノート

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