N-((N-Methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino)carbonyl)-L-valine Methyl Ester → N-((N-methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino)carbonyl)-L-valine

HRID 53930Notes

Reaction equation

HRID 53930 reaction equation
C[O:2][C:3](=[O:22])[C@H:4]([CH:19]([CH3:21])[CH3:20])[NH:5][C:6]([N:8]([CH3:18])[CH2:9][C:10]1[N:11]=[C:12]([CH:15]([CH3:17])[CH3:16])[O:13][CH:14]=1)=[O:7]>O1CCOCC1.O>[CH3:18][N:8]([C:6]([NH:5][C@H:4]([C:3]([OH:22])=[O:2])[CH:19]([CH3:20])[CH3:21])=[O:7])[CH2:9][C:10]1[N:11]=[C:12]([CH:15]([CH3:17])[CH3:16])[O:13][CH:14]=1

Participants

4

Reactant 1

HCID 10614961N-((N-Methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino)carbonyl)-L-valine Methyl Ester

Product 1

HCID 10851544N-((N-methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino)carbonyl)-L-valineYield 98.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-((N-methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino)carbonyl)-L-valine methyl ester 10 (0.511 g, 0.00164 mol) in p-dioxane (10 mL) and H2O (5 mL) was added LiOH monohydrate (0.103 g, 0.00246 mol). After stirring at room temperature for 1 hr, the p-dioxane was removed by rotary evaporation in vacuo, and the remaining aqueous solution was treated with 1N aq HCl (2.46 mL) and extracted with ethyl acetate (4×100 mL). The combined organic extract was washed with saturated brine and dried for 15 mins over Na2SO4. Concentration in vacuo followed by CH2Cl2 chases (2x) afforded the desired compound as a white solid (0.480 g, 0.00161 mol, 98%): 1H NMR (DMSO-d6) δ 0.90 (dd, J1 =6.9 Hz, J2 =2.4 Hz, 6H), 1.24 (d, J=6.9 Hz, 6H), 1.99-2.12 (m, 1H), 2.83 (s, 3H), 2.96-3.10 (m, 1H), 3.96 (dd, J1 =8.4 Hz, J2 =6 Hz, 1H), 4.19-4.32 (m, 2H), 6.26 (d, J=8.4 Hz, 1H), 7.80 (s, 1H). Mass spectrum: (M+H)+ =298

Workup

  1. customthe p-dioxane was removed by rotary evaporation in vacuo
  2. additionthe remaining aqueous solution was treated with 1N aq HCl (2.46 mL)
  3. extractionextracted with ethyl acetate (4×100 mL)
  4. extractionThe combined organic extract
  5. washwas washed with saturated brine
  6. dry with materialdried for 15 mins over Na2SO4
  7. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-770818230dc54aebbe42d3d0624d709d
Source dataset
uspto-grants-1997_04
Patent number
US05621109

Reaction notes

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