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

HRID 547882

反応式

HRID 547882 の反応式
[CH3:1][C:2]([NH:16]C(=O)OC(C)(C)C)([CH3:15])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]1=[O:14].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>[NH2:16][C:2]([CH3:15])([CH3:1])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]1=[O:14]

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 8857Ethyl Acetate溶媒HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-060a98dad3504ba0ab5ede5dc0e8435b
出典データセット
uspto-grants-2011_05
特許番号
US07939658B2

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