2(3H)-Benzoxazolone → Tert-butyl [1,1-dimethyl-3-(2-oxobenzooxazol-3-yl)propyl]carbamate

HRID 33373

반응식

HRID 33373 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[O:10].[H-].[Na+].N[CH2:14][CH2:15][C:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:18])[CH3:17].C(=O)([O-])O.[Na+]>CN1C(=O)N(C)CCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH3:18][C:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:17])[CH2:15][CH2:14][N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1][C:2]1=[O:10]

참가 물질

8

반응물 4

HCID 60432(3H)-BenzoxazoloneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 45072487tert-butyl N-(4-amino-2-methylbutan-2-yl)carbamate

생성물 1

HCID 57435843Tert-butyl [1,1-dimethyl-3-(2-oxobenzooxazol-3-yl)propyl]carbamate

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 8857Ethyl Acetate용매HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-용매

실험 절차

4.0 g (29.6 mmol) benzoxazol-2-one are dissolved in 40 mL DMPU and cooled with an ice bath. Under protective gas 897 mg (95%; 35.5 mmol) sodium hydride are added batchwise to this solution. The reaction mixture is heated to ambient temperature and then stirred for another hour. 9.85 g (44.4 mmol) tert-butyl (3-amino-1,1-dimethyl-propyl)-carbamate and 1.97 g (5.3 mmol) tetrabutylammonium iodide are added and the mixture is stirred overnight. The reaction is stopped by the careful addition of sodium hydrogen carbonate solution. Ethyl acetate is added, the aqueous phase is separated off and extracted repeatedly with ethyl acetate. The combined organic phases are washed with sodium chloride solution, dried with sodium sulphate and evaporated down. Purification of the residue by column chromatography (silica gel; petroleum ether/ethyl acetate=7:3) yields the desired product in the form of an oil. Yield 4.1 g (43%); mass spectroscopy: [M+H]+=321.

후처리

  1. temperaturecooled with an ice bath
  2. stirringthe mixture is stirred overnight
  3. customthe aqueous phase is separated off
  4. extractionextracted repeatedly with ethyl acetate
  5. washThe combined organic phases are washed with sodium chloride solution
  6. dry with materialdried with sodium sulphate
  7. customevaporated down
  8. customPurification of the residue by column chromatography (silica gel; petroleum ether/ethyl acetate=7:3)

출처 및 근거

ORD 기록
ord-ca636d061a034eb9a8bc2731eb253416
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429583B2

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