Methyl iodide → tert-butyl N-[(2S)-2-methoxypropyl]carbamate

HRID 246124노트

반응식

HRID 246124 반응식
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][C@@H:9]([OH:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].I[CH3:14]>C(#N)C.[Ag]=O>[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][C@@H:9]([O:11][CH3:14])[CH3:10])([CH3:2])([CH3:4])[CH3:3]

참가 물질

5

반응물 2

HCID 6328Methyl iodide2회HCID 11789722N-Boc-(S)-1-amino-2-propanol

생성물 1

HCID 86643351tert-butyl N-[(2S)-2-methoxypropyl]carbamate수율 32%

시약·촉매·용매 2

HCID 92152Silver(II) oxide촉매2회HCID 6342Acetonitrile용매

실험 절차

((S)-2-Hydroxy-propyl)-carbamic acid tert-butyl ester (0.25 g, 1.43 mmol) was dissolved in acetonitrile (14 ml) and iodomethane (1.78 ml, 28.5 mmol), and then silver oxide (0.53 g, 2.28 mmol; prepared as in Org. Syn. Coll. Vol. VII, p. 386) were added. The reaction flask was covered to protect from light and the reaction was heated at reflux for 24 h. Additional iodomethane (1.8 ml) and silver oxide (0.26 g) were added and heating was continued until the reaction was judged to be complete by standard reverse phase LC/MS. The reaction mixture was filtered through diatomaceous earth, rinsing with ethyl acetate. After evaporation the residue was purified by silica gel chromatography (ethyl acetate/hexanes) to give 85 mg (32%) of ((S)-2-methoxy-propyl)-carbamic acid tert-butyl ester. (M+Na)+=212.

후처리

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 24 h
  3. temperatureheating
  4. filtrationThe reaction mixture was filtered through diatomaceous earth
  5. washrinsing with ethyl acetate
  6. customAfter evaporation the residue
  7. customwas purified by silica gel chromatography (ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-8412e720ae5945539cdf385cac254d75
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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