Water → 4-cyclopentyl-7-methoxycarbonyl-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine

HRID 234901노트

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HRID 234901 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[NH:9][C:10](=[O:14])[CH:11]([CH3:13])[O:12][C:7]=2[CH:6]=1)=[O:4].[H-].[Na+].[CH:19]1(Br)[CH2:23][CH2:22][CH2:21][CH2:20]1.O>CN(C)C=O.C(OCC)(=O)C>[CH:19]1([N:9]2[C:8]3[CH:15]=[CH:16][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][C:7]=3[O:12][CH:11]([CH3:13])[C:10]2=[O:14])[CH2:23][CH2:22][CH2:21][CH2:20]1

참가 물질

7

반응물 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 10798997methyl 2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-7-carboxylate

생성물 1

HCID 233531674-cyclopentyl-7-methoxycarbonyl-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine수율 51.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

To a solution of 7-methoxycarbonyl-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (prepared in Preparation 1) (4.0 g) in dimethylformamide (80 ml) were added 60% sodium hydride (in oil) (0.73 g) and cyclopentyl bromide (2.5 g) and the mixture was stirred at 70° C. for a day. Water was added to the reaction solution and extraction with ethyl acetate was conducted. The solvent was distilled off under reduced pressure and the resulting residue was subjected to purification by column chromatography using chloroform to give 4-cyclopentyl-7-methoxycarbonyl-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (2.5 g) as an oil.

후처리

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe resulting residue was subjected to purification by column chromatography

출처 및 근거

ORD 기록
ord-66735cc8d2c34e6c9af0710ea4e9f539
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05597820

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