Sodium Hydroxide → 4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-ylamine

HRID 1611939노트

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HRID 1611939 반응식
COC(=O)[NH:4][C:5]1[O:6][C:7]2[C:13]([CH:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[CH:12][CH:11]=[C:10]([O:20][CH3:21])[C:8]=2[N:9]=1.[OH-].[Na+]>O1CCOCC1.C(O)CO>[CH3:21][O:20][C:10]1[C:8]2[N:9]=[C:5]([NH2:4])[O:6][C:7]=2[C:13]([CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:12][CH:11]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 23593640[4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-carbamic acid methyl ester

생성물 1

HCID 222522334-Methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-ylamine수율 74.1%

시약·촉매·용매 2

HCID 174Ethylene Glycol용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

To a stirred solution of 130 g (4.24 mmol) [4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-carbamic acid methyl ester in 90 ml dioxane and 30 ml ethylene glycol was added 90 ml of a 5 N aq. sodium hydroxide solution, and the mixture was heated at 100° C. for 16 h. After cooling to room temperature, the mixture was poured onto water and extracted four times with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated in vacuo. Flash chromatography (dichloromethane then 5/95 methanol/dichloromethane) afforded 0.78 g (74%) 4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-ylamine as a brown solid. ES-MS m/e (%): 249 (M+H+, 100).

후처리

  1. temperatureAfter cooling to room temperature
  2. additionthe mixture was poured onto water
  3. extractionextracted four times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f82c0e72b049405cba7fa3830faa2dc1
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06992083B2

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