Lithium Hydroxide → (2S)-3-Methyl-2-({[methyl(pent-4-en-1-yl)amino]carbonyl}amino)butanoic acid

HRID 1360107Notes

Reaction equation

HRID 1360107 reaction equation
[CH3:1][CH:2]([CH3:18])[C@H:3]([NH:8][C:9]([N:11]([CH3:17])[CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16])=[O:10])[C:4]([O:6]C)=[O:5].[Li+].[OH-]>C1COCC1>[CH3:1][CH:2]([CH3:18])[C@H:3]([NH:8][C:9]([N:11]([CH3:17])[CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16])=[O:10])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57617072Methyl (2S)-3-methyl-2-({[methyl(pent-4-en-1-yl)amino]carbonyl}amino)butanoate

Product 1

HCID 57617111(2S)-3-Methyl-2-({[methyl(pent-4-en-1-yl)amino]carbonyl}amino)butanoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 250 mL round bottom flask under nitrogen was charged with methyl (2S)-3-methyl-2-({[methyl(pent-4-en-1-yl)amino]carbonyl}amino)butanoate from the previous step, THF (40 mL), and aqueous LiOH (1 M, 60 mmol, 60 mL). The reaction mixture was stirred 18 hours. THF was removed by evaporation. The remaining aqueous mixture was poured into water and washed once with EtOAc. The aqueous layer was acidified with 1 M hydrochloric acid and extracted with EtOAc (3×). Combined organic extracts were dried with anhydrous NaSO4, filtered and evaporated to give the title compound as a pale oil (2.34 g, 9.66 mmol, 95%). LRMS m/e [M+H]+ 243.

Workup

  1. customTHF was removed by evaporation
  2. additionThe remaining aqueous mixture was poured into water
  3. washwashed once with EtOAc
  4. extractionextracted with EtOAc (3×)
  5. dry with materialCombined organic extracts were dried with anhydrous NaSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-6f875324f5ce4552b958e58cd1965207
Source dataset
uspto-grants-2011_02
Patent number
US07879797B2

Reaction notes

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