Water → HCID 86606497, 화합물

HRID 1994126노트

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HRID 1994126 반응식
[OH:1][CH2:2][C@@H:3]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[H-].[Na+].[CH3:23]I.O>C1COCC1>[CH3:23][O:1][CH2:2][C@@H:3]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:10])([CH3:11])[CH3:9]

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86606496tert-butyl N-[(2S)-1-{[(tert-butoxy)carbonyl]amino}-3-hydroxypropan-2-yl]carbamate

생성물 1

HCID 86606497HCID 86606497, 화합물수율 36.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of di-tert-butyl [(2S)-3-hydroxypropane-1,2-diyl]biscarbamate (2.45 g, 8.10 mmol) in THF (80 mL) at 0° C., was added NaH (60%, 357 mg, 8.91 mmol). The reaction was allowed to stir at 0° C. for 30 min, and then methyl iodide (0.556 mL, 8.91 mmol) was added dropwise. The reaction was stirred at 0° C. for 1 h and then allowed to warm to rt and stirred for 3 h. Water was added and the reaction was extracted into EtOAc. The combined organic solutions were washed with brine, dried (Na2SO4) and evaporated. The residue was purified by chromatography (SiO2, EtOAc/hexane) to yield the title compound as a white solid (895 mg, 36%).

후처리

  1. stirringThe reaction was stirred at 0° C. for 1 h
  2. temperatureto warm to rt
  3. stirringstirred for 3 h
  4. extractionthe reaction was extracted into EtOAc
  5. washThe combined organic solutions were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe residue was purified by chromatography (SiO2, EtOAc/hexane)

출처 및 근거

ORD 기록
ord-ee55feace5ac4ee39d56176525e8efc7
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652041B2

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