Triethylamine → Tert-butyl 5-oxo-1,4-oxazepane-4-carboxylate

HRID 45584노트

반응식

HRID 45584 반응식
[O:1]1[CH2:7][CH2:6][C:5](=[O:8])[NH:4][CH2:3][CH2:2]1.[C:9]([O:13][C:14](=O)[O:15]C(C)(C)C)([CH3:12])([CH3:11])[CH3:10].CN(C1C=CC=CN=1)C.C(N(CC)CC)C>ClCCl.O>[O:8]=[C:5]1[CH2:6][CH2:7][O:1][CH2:2][CH2:3][N:4]1[C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 70230201,4-Oxazepan-5-oneHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

생성물 1

HCID 68190041Tert-butyl 5-oxo-1,4-oxazepane-4-carboxylate수율 465%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 1,4-oxazepan-5-one (6.9 g, 60.0 mmol) in dichloromethane (120.0 mL) were added di-tert-butylcarbonate (1.75 g, 8.00 mmol) and dimethylaminopyridine (7.90 g, 65.0 mmol), and triethylamine (12.5 mL, 90.0 mmol) was added dropwise. After stirring for 16 hours at room temperature, to the mixture was added water, and the aqueous layer was extracted with chloroform. The organic layer was washed with saturated aqueous solution of ammonium chloride and brine, and then dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified with silica gel column (hexane/ethyl acetate=90/10 to 0/100) to give the title compound (7.30 g, 37.2 mmol, 62%).

후처리

  1. additionwas added dropwise
  2. extractionthe aqueous layer was extracted with chloroform
  3. washThe organic layer was washed with saturated aqueous solution of ammonium chloride and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified with silica gel column (hexane/ethyl acetate=90/10 to 0/100)

출처 및 근거

ORD 기록
ord-8c00a6bebe7d4434a005fa03dc9abcc2
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541585B2

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