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Water → Methyl 3-methyl-2-(3-(4-(2-oxo-2-(3-(trifluoromethyl)phenylamino) acetamido)phenyl)isoxazole-5-carboxamido)butanoate

HRID 75851
ノート
印刷プレビュー

反応式

HRID 75851 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:23]=[C:22]([C:24]([NH:26][CH:27]([CH:32]([CH3:34])[CH3:33])[C:28]([O:30][CH3:31])=[O:29])=[O:25])[O:21][N:20]=2)=[CH:15][CH:14]=1.[OH2:35].CCO[C:39]([CH3:41])=[O:40]>C(Cl)(=O)C(Cl)=O>[CH3:33][CH:32]([CH3:34])[CH:27]([NH:26][C:24]([C:22]1[O:21][N:20]=[C:19]([C:16]2[CH:17]=[CH:18][C:13]([NH:12][C:39](=[O:40])[C:41](=[O:35])[NH:6][C:5]3[CH:7]=[CH:8][CH:9]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=3)=[CH:14][CH:15]=2)[CH:23]=1)=[O:25])[C:28]([O:30][CH3:31])=[O:29]
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 4

HCID 962WaterHCID 73753-(Trifluoromethyl)anilineHCID 8857Ethyl AcetateHCID 67352790Methyl 2-(3-(4-aminophenyl)isoxazole-5-carboxamido)-3-methylbutanoate

生成物 1

HCID 67353582Methyl 3-methyl-2-(3-(4-(2-oxo-2-(3-(trifluoromethyl)phenylamino) acetamido)phenyl)isoxazole-5-carboxamido)butanoate収率 29%

試薬・触媒・溶媒 1

HCID 65578Oxalyl chloride溶媒

実験手順

To 3-(trifluoromethyl)aniline (0.117 ml), methyl 2-(3-(4-aminophenyl)isoxazole-5-carboxamido)-3-methylbutanoate (300 mg, example 151, step 3) in EtOAc (6 ml), oxalyl chloride was added and stirred at RT for 3 hours. To this water was added and organic layer was collected and dried over Na2SO4 and concentrated to obtain brown solid which was purified by column chromatography (silica gel, EtOAc—CHCl3 to obtain pale brown solid which was crystallized from DCM-Petroleum ether to yield 150 mg (29%) of the title compound as off white solid. MS (ES+): m/z 533 (M+1); 1HNMR (DMSO-d6; 300 MHz): δ 11.24 (s, 1H), 11.14 (s, 1H), 9.25 (d, 1H), 8.35 (dd, 1H), 8.16 (dd, 1H), 8.06 (d, 2H), 7.96 (d, 2H), 7.72 (s, 1H), 7.64 (m, 1H), 7.54 (dd, 1H), 4.31 (m, 1H), 3.68 (s, 3H), 2.23 (m, 1H), 0.97 (d, 6H).

後処理

  1. customorganic layer was collected
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto obtain brown solid which
  5. customwas purified by column chromatography (silica gel, EtOAc—CHCl3
  6. customto obtain pale brown solid which
  7. customwas crystallized from DCM-Petroleum ether

出典と根拠

ORDレコード
ord-574ec6e76d6248ebb9703b9165ef265e
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08835428B2

反応ノート

読み込み中…

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