Water → 3-Methyl-N-[(pent-4-en-1-yl)(propan-2-yl)carbamoyl]-L-valine

HRID 2377641노트

반응식

HRID 2377641 반응식
[CH:1]([N:4]([CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21])[C:5]([NH:7][C@H:8]([C:13]([O:15]C)=[O:14])[C:9]([CH3:12])([CH3:11])[CH3:10])=[O:6])([CH3:3])[CH3:2].O.[Li+].[OH-]>O1CCOCC1>[CH:1]([N:4]([CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21])[C:5]([NH:7][C@H:8]([C:13]([OH:15])=[O:14])[C:9]([CH3:12])([CH3:11])[CH3:10])=[O:6])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57692708Methyl N-{[isopropyl(pent-4-en-1-yl)amino]carbonyl}-3-methyl-L-valinate

생성물 1

HCID 576926803-Methyl-N-[(pent-4-en-1-yl)(propan-2-yl)carbamoyl]-L-valine

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution (0.1 M) of methyl N-{[isopropyl(pent-4-en-1-yl)amino]carbonyl}-3-methyl-L-valinate in a 1:1 mixture of water and dioxane, LiOH (4 eq) was added and the resulting mixture was stirred at room temperature for 6 h. The reaction mixture was then concentrated at reduced pressure and the crude residue was dissolved in EtOAc. The organic phase was washed with water. The aqueous phase was brought to pH=2 and re-extracted with EtOAc. After drying over Na2SO4 and evaporation of the volatiles, N-{[isopropyl(pent-4-en-1-yl)amino]carbonyl}-3-methyl-L-valine was recovered as a brownish solid (100%) and used without any further purification. LRMS (ESI) m/z 285 [(M+H)+; calcd for C15H29N2O3: 285.2].

후처리

  1. additionwas added
  2. concentrationThe reaction mixture was then concentrated at reduced pressure
  3. dissolutionthe crude residue was dissolved in EtOAc
  4. washThe organic phase was washed with water
  5. extractionre-extracted with EtOAc
  6. dry with materialAfter drying over Na2SO4 and evaporation of the volatiles, N-{[isopropyl(pent-4-en-1-yl)amino]carbonyl}-3-methyl-L-valine
  7. customwas recovered as a brownish solid (100%)
  8. customused without any further purification

출처 및 근거

ORD 기록
ord-03734799bdf947c699398436398cb728
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07470664B2

반응 노트

불러오는 중…