4-Nitrophenyl chloroformate → (R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2-dihydro-imidazo[4,5-c]quinolin-3-yl)-piperidine-1-carboxylate

HRID 643153ノート

反応式

HRID 643153 の反応式
Cl[C:2](OC1C=CC([N+]([O-])=O)=CC=1)=[O:3].[CH2:14]([O:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([CH2:29][C@@H:30]([OH:35])[C:31]([O:33][CH3:34])=[O:32])=[CH:24][C:23]=1[CH3:36])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH:37]1[CH2:42][CH2:41][CH:40]([N:43]2[C:47]3[CH:48]=[N:49][C:50]4[CH:51]=[CH:52][CH:53]=[CH:54][C:55]=4[C:46]=3[NH:45][C:44]2=[O:56])[CH2:39][CH2:38]1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[O:56]=[C:44]1[N:43]([CH:40]2[CH2:39][CH2:38][N:37]([C:2]([O:35][C@@H:30]([C:31]([O:33][CH3:34])=[O:32])[CH2:29][C:25]3[CH:24]=[C:23]([CH3:36])[C:22]([O:21][CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[C:27]([CH3:28])[CH:26]=3)=[O:3])[CH2:42][CH2:41]2)[C:47]2[CH:48]=[N:49][C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][C:55]=3[C:46]=2[NH:45]1

参加物

6

反応物 3

HCID 821294-Nitrophenyl chloroformateHCID 183215593-Piperidin-4-yl-1,3-dihydroimidazo[4,5-c]quinolin-2-oneHCID 67273374methyl(R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-hydroxy-propionate

生成物 1

HCID 68676084(R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-methoxycarbonyl-ethyl 4-(2-oxo-1,2-dihydro-imidazo[4,5-c]quinolin-3-yl)-piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒2 回

実験手順

Under a nitrogen atmosphere 1.28 g (6.36 mmol) 4-nitrophenyl chloroformate were added at RT to a solution of 0.78 g (6.36 mmol) 4-dimethylaminopyridine in 100 mL pyridine and the mixture was stirred for 1 h at RT. Then a solution of 2.00 g (6.36 mmol) methyl (R)-3-(4-benzyloxy-3,5-dimethyl-phenyl)-2-hydroxy-propionate in 20 mL pyridine was added dropwise at RT and the reaction mixture was stirred for 2 h after the end of the addition. Then 1.71 g (6.36 mmol) 3-piperidin-4-yl-1,3-dihydro-imidazo[4,5-c]quinoline-2-one was added to the reaction mixture, which was then heated to 100° C. for 4 h. The precipitate formed was filtered off, the filtrate was evaporated down i.vac., the residue was mixed with 200 mL EtOAc and 200 mL semisaturated KHSO4 solution, the product being obtained as a precipitate. This was suction filtered and dried.

後処理

  1. stirringthe reaction mixture was stirred for 2 h
  2. additionafter the end of the addition
  3. temperaturewas then heated to 100° C. for 4 h
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. customthe filtrate was evaporated down i.vac
  7. addition, the residue was mixed with 200 mL EtOAc and 200 mL semisaturated KHSO4 solution
  8. customthe product being obtained as a precipitate
  9. filtrationThis was suction filtered
  10. customdried

出典と根拠

ORDレコード
ord-8b38c85137d74a43a2fc2a9d1393bcd4
出典データセット
uspto-grants-2010_04
特許番号
US07696209B2

反応ノート

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