Lithium Hydroxide → 4-(4-{[(1,1-Dimethylethyl)oxy]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)benzoic acid

HRID 473921노트

반응식

HRID 473921 반응식
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][C:15]=3[CH:28]=2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Li+]>O1CCCC1.O>[CH3:27][C:24]([O:23][C:21]([N:17]1[CH2:16][C:15]2[CH:28]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][CH:9]=3)[CH:12]=[CH:13][C:14]=2[O:20][CH2:19][CH2:18]1)=[O:22])([CH3:25])[CH3:26]

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 668201301,1-dimethylethyl 7-{4-[(methyloxy)carbonyl]phenyl}-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

생성물 1

HCID 675140494-(4-{[(1,1-Dimethylethyl)oxy]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)benzoic acid수율 85%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a slurry of 1,1-dimethylethyl 7-{4-[(methyloxy)carbonyl]phenyl}-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (9.8 g, 26 mmol) in tetrahydrofuran (40 mL) was added a solution of lithium hydroxide (3.1 g, 130 mmol) in water (15 mL). The resulting mixture was heated at 60° C. for 18 h then partitioned between ethyl acetate (100 mL) and 1M hydrochloric acid (50 mL). The organic layer was washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by silica gel column chromatography (5% methanol in dichloromethane) provided 4-(4-{[(1,1-dimethylethyl)oxy]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)benzoic acid (8.1 g, 85% yield). MS (EI) for C21H23NO5: 370 (MH+).

후처리

  1. customthen partitioned between ethyl acetate (100 mL) and 1M hydrochloric acid (50 mL)
  2. washThe organic layer was washed with brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel column chromatography (5% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-61d27ab364bc4a94a43d630ed7eea382
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637499B2

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