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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
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HRID 75851 반응식
[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]
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 65578Oxalyl chloride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-574ec6e76d6248ebb9703b9165ef265e
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08835428B2

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