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Toluene → Isopropyl 4-{5-[2-fluoro-4-(methylsulfonyl)phenyl]benzo[d]oxazol-2-yl}piperidine-1-carboxylate

HRID 710120
ノート
印刷プレビュー

反応式

HRID 710120 の反応式
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:14]=[C:13]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:12]=[CH:11][C:10]=1[C:19]1[CH:20]=[CH:21][C:22]2[O:26][C:25]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[N:24][C:23]=2[CH:33]=1.Cl[C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36].C1(C)C=CC=CC=1>C(Cl)Cl.O>[F:8][C:9]1[CH:14]=[C:13]([S:15]([CH3:18])(=[O:16])=[O:17])[CH:12]=[CH:11][C:10]=1[C:19]1[CH:20]=[CH:21][C:22]2[O:26][C:25]([CH:27]3[CH2:32][CH2:31][N:30]([C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36])[CH2:29][CH2:28]3)=[N:24][C:23]=2[CH:33]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 1140TolueneHCID 7917Isopropyl chloroformateHCID 710895675-(2-Fluoro-4-(methylsulfonyl)phenyl)-2-(piperidin-4-yl)-benzo[d]oxazole 2,2,2-trifluoroacetate

生成物 1

HCID 71114585Isopropyl 4-{5-[2-fluoro-4-(methylsulfonyl)phenyl]benzo[d]oxazol-2-yl}piperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6344
Dichloromethane
溶媒

実験手順

Tert-butyl 4-{5-[2-fluoro-4-(methylsulfonyl)phenyl]benzo[d]oxazol-2-yl}piperidine-1-carboxylate (200 mg, 0.42 mmol) dissolved in DCM and added Trifluoroacetic acid (0.75 ml). This mixture was stirred at rt for 2 h. DCM removed from the reaction mixture to obtain 5-(2-fluoro-4-(methylsulfonyl)phenyl)-2-(piperidin-4-yl)benzo[d]oxazole 2,2,2-trifluoroacetate (190 mg). 5-(2-fluoro-4-(methylsulfonyl)phenyl)-2-(piperidin-4-yl)-benzo[d]oxazole 2,2,2-trifluoroacetate (190 mg, 0.39 mmol) was dissolved in DCM (20 ml) and added TEA (0.43 ml, 3.12 mmol). This mixture stirred at rt for 30 mins and added isopropyl chloroformate in toluene (0.095 g, 0.78 mmol). After 1 h, reaction mass diluted with water and extracted with DCM. Removal of DCM afforded crude. Crude was purified by combiflash using a mixture of EtOAc and Petether (35:65) as eluent to afford the titled compound (120 mg) as a pale-yellow solid. M.P.: 96.5-101.2° C. 1H-NMR (δ ppm, CDCl3, 400 MHz): 7.87 (s, 1H), 7.81 (dd, J 1.7, 8, 1H), 7.80-7.75 (m, 1H), 7.67 (t, J 7.5, 1H), 7.59 (d, J 8.4, 1H), 7.50 (d, J 8.5, 1H), 4.94 (septet, J 6.2, 1H), 4.19 (d, J 10.9, 2H), 3.22-3.13 (m, 1H), 3.12 (s, 3H), 3.04 (t, J 10.9, 2H), 2.22-2.14 (m, 2H), 2.00-1.88 (m, 2H), 1.26 (d, J 6.2, 6H).

後処理

  1. waitAfter 1 h
  2. customreaction mass
  3. extractionextracted with DCM
  4. customRemoval of DCM
  5. customafforded crude
  6. customCrude was purified by combiflash
  7. additiona mixture of EtOAc and Petether (35:65) as eluent

出典と根拠

ORDレコード
ord-796888eebeb84f64ab41732ea74beedd
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181214B2

反応ノート

読み込み中…

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