Trifluoroacetic acid → 3-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one trifluoroacetate

HRID 1407437노트

반응식

HRID 1407437 반응식
C([SiH](CC)CC)C.O[C:9]1([C:25]2[C:35]([OH:36])=[CH:34][C:28]3[N:29]([CH3:33])[CH2:30][CH2:31][O:32][C:27]=3[CH:26]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][C@H:19]2[CH2:23][CH2:22][CH2:21][O:20]2)[C:10]1=[O:24].[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]>ClCCl>[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40].[OH:36][C:35]1[C:25]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C@H:19]3[CH2:23][CH2:22][CH2:21][O:20]3)[C:10]2=[O:24])=[CH:26][C:27]2[O:32][CH2:31][CH2:30][N:29]([CH3:33])[C:28]=2[CH:34]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 685987153-hydroxy-3-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one

생성물 1

HCID 685974793-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one trifluoroacetate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a cooled (0° C.) solution of triethylsilane (1.3 mL, 8.2 mmol) in trifluoroacetic acid (8 mL) was added dropwise a solution of 3-hydroxy-3-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one (1.04 g, 2.62 mmol) in dichloromethane (3 mL). The resulting solution was warmed to reflux and stirred under nitrogen for 90 min. Once cooled, the solvent was removed under reduced pressure to afford 3-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one trifluoroacetate as a light brown foam: MS (ES+) m/z 381.0 (M+1).

후처리

  1. temperatureThe resulting solution was warmed
  2. temperatureto reflux
  3. temperatureOnce cooled
  4. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-87833560f2d04096acebb149a58e2719
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916580B2

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