2(3H)-Benzoxazolone → 3-(3-amino-3-methyl-butyl)-3H-benzoxazol-2-one

HRID 493081

반응식

HRID 493081 반응식
C(OC(=O)[NH:7][C:8]([CH3:22])([CH3:21])[CH2:9][CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][C:12]1=[O:20])(C)(C)C.O1C2C=CC=CC=2NC1=O.[H-].[Na+].NCCC(NC(=O)OC(C)(C)C)(C)C.C(=O)([O-])O.[Na+]>CN1C(=O)N(C)CCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[NH2:7][C:8]([CH3:22])([CH3:21])[CH2:9][CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][C:12]1=[O:20]

참가 물질

9

반응물 5

HCID 60432(3H)-BenzoxazoloneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 45072487tert-butyl N-(4-amino-2-methylbutan-2-yl)carbamateHCID 57435843Tert-butyl [1,1-dimethyl-3-(2-oxobenzooxazol-3-yl)propyl]carbamate

생성물 1

HCID 574358383-(3-amino-3-methyl-butyl)-3H-benzoxazol-2-one

시약·촉매·용매 3

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

실험 절차

tert-butyl[1,1-dimethyl-3-(2-oxo-benzoxazol-3-yl)-propyl]-carbamate: 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 is 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. 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-829931ec9cb540ec95496c98b668fbba
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534789B2

연결된 노트

불러오는 중…