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

HRID 473921ノート

反応式

HRID 473921 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-61d27ab364bc4a94a43d630ed7eea382
出典データセット
uspto-grants-2014_01
特許番号
US08637499B2

反応ノート

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