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

HRID 2377641ノート

反応式

HRID 2377641 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-03734799bdf947c699398436398cb728
出典データセット
uspto-grants-2008_12
特許番号
US07470664B2

反応ノート

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