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

HRID 1511589Notes

Reaction equation

HRID 1511589 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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].

Workup

  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

Sources & evidence

ORD record
ord-1069302d9e99495d8711e72067657435
Source dataset
uspto-grants-2012_07
Patent number
US08216999B2

Reaction notes

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