1,2-Dichloroethane → Tert-butyl 4-(2-{(cyclohexylcarbonyl) [(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]amino}-1-phenylethyl)piperidine-1-carboxylate

HRID 1943027ノート

反応式

HRID 1943027 の反応式
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH2:12][NH:13][CH2:14][CH:15]([CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:3]1=[O:35].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH:59]1([C:65](O)=[O:66])[CH2:64][CH2:63][CH2:62][CH2:61][CH2:60]1>C(Cl)Cl>[CH:59]1([C:65]([N:13]([CH2:12][C:4]2[C:3](=[O:35])[N:2]([CH3:1])[C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:14][CH:15]([CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:24][CH2:23]2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:66])[CH2:64][CH2:63][CH2:62][CH2:61][CH2:60]1

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 7413Cyclohexanecarboxylic acidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 58415941Tert-butyl 4-(2-{[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]amino}-1-phenylethyl)piperidine-1-carboxylate

生成物 1

HCID 58415912Tert-butyl 4-(2-{(cyclohexylcarbonyl) [(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]amino}-1-phenylethyl)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

tert-butyl 4-(2-{[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]amino}-1-phenylethyl)piperidine-1-carboxylate (1.61 g crude, 3.39 mmol), EDC (1.298 g, 6.77 mmol), HOAT (0.461 g, 3.39 mmol), DIEA (1.182 ml, 6.77 mmol), and cyclohexanecarboxylic acid (0.504 ml, 4.06 mmol) were combined in CH2Cl2 and the reaction stirred for 15 hours. The mixture was partitioned between CH2Cl2 and satd. bicarb, the aqueous portion extracted 3×CH2Cl2, and the organic portion dried (Na2SO4) then concentrated in vacuo. The resulting material was purified by silica gel chromatography on an Isco Companion. The desired fractions were combined and concentrated in vacuo. 1.63 g, 82% over two steps.

後処理

  1. customThe mixture was partitioned between CH2Cl2 and satd
  2. extractionbicarb, the aqueous portion extracted 3×CH2Cl2
  3. dry with materialthe organic portion dried (Na2SO4)
  4. concentrationthen concentrated in vacuo
  5. customThe resulting material was purified by silica gel chromatography on an Isco Companion
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-dd00ba19f87b40e5b7bac85a36329e7d
出典データセット
uspto-grants-2013_03
特許番号
US08389720B2

反応ノート

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