Lithium Hydroxide → 3-Methyl-N-[methyl(pent-4-en-1-yl)carbamoyl]-L-valine

HRID 1511561Notes

Reaction equation

HRID 1511561 reaction equation
[CH3:1][C:2]([CH3:19])([CH3:18])[C@@H:3]([C:14]([O:16]C)=[O:15])[NH:4][C:5]([N:7]([CH3:13])[CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])=[O:6].[OH-].[Li+]>O1CCCC1>[CH3:1][C:2]([CH3:19])([CH3:18])[C@@H:3]([C:14]([OH:16])=[O:15])[NH:4][C:5]([N:7]([CH3:13])[CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])=[O:6]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59856469Methyl 3-methyl-N-[methyl(pent-4-en-1-yl)carbamoyl]-L-valinate

Product 1

HCID 574311913-Methyl-N-[methyl(pent-4-en-1-yl)carbamoyl]-L-valineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-methyl-N-{[methyl(pent-4-enyl)amino]carbonyl}-L-valinate (3.00 g, 11.2 mmol), lithium hydroxide (1M, 56.0 mL, 56.0 mmol) in tetrahydrofuran (40 mL) was heated to 50° C. for 1 h. Contents of the reaction flask were cooled and evaporated to remove tetrahydrofuran. The remaining mixture was poured into 5% potassium bisulfate and extracted with methylene chloride (3×10 mL). The combined organic extracts were dried with anhydrous sodium sulfate, filtered and evaporated to give the title compound as a colorless oil, 2.87 g (100% yield). LRMS (ESI) m/z 257 [(M+H)+; calcd for C13H25N2O3: 257].

Workup

  1. temperatureContents of the reaction flask were cooled
  2. customevaporated
  3. customto remove tetrahydrofuran
  4. additionThe remaining mixture was poured into 5% potassium bisulfate
  5. extractionextracted with methylene chloride (3×10 mL)
  6. dry with materialThe combined organic extracts were dried with anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-1b5d566f634e4402978552a082899208
Source dataset
uspto-grants-2012_07
Patent number
US08216999B2

Reaction notes

Loading…