1-(2-isopropyloxazol-4-yl)-N-methylmethanamine → N-((N-Methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino)carbonyl)-L-valine Methyl Ester

HRID 1858461Notes

Reaction equation

HRID 1858461 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH:18]([CH3:20])[CH3:19])[NH:5][C:6]([O:8]C1C=CC([N+]([O-])=O)=CC=1)=O.[CH:22]([C:25]1[O:26][CH:27]=[C:28]([CH2:30][NH:31][CH3:32])[N:29]=1)([CH3:24])[CH3:23]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH:18]([CH3:19])[CH3:20])[NH:5][C:6]([N:31]([CH3:32])[CH2:30][C:28]1[N:29]=[C:25]([CH:22]([CH3:23])[CH3:24])[O:26][CH:27]=1)=[O:8]

Participants

4

Reactant 2

HCID 108207841-(2-isopropyloxazol-4-yl)-N-methylmethanamineHCID 15344176Methyl N-[(4-nitrophenoxy)carbonyl]-L-valinate

Product 1

HCID 10614961N-((N-Methyl-N-((2-isopropyl-4-oxazolyl)methyl)amino)carbonyl)-L-valine Methyl EsterYield 54.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-(((4-nitrophenyl)oxy)carbonyl)-L-valine methyl ester (0.903 g, 0.00305 mol) in anhydrous DMF (6 mL) was added to a solution of 2-isopropyl-4-(((N-methyl)amino)methyl)oxazole (9, 0.470 g, 0.00305 mol) in anhydrous DMF (6 mL) under argon, and the yellow solution was stirred at room temperature for 30 min. Solvent was removed by rotary evaporation in vacuo and the resulting oil dried on high vacuum for 1 hr. The residue was applied to a 150 g SiO2 flash column and eluted with 20% EtOAc/CH2Cl2 and 3% MeOH/CH2Cl2. The material obtained after concentration of the product fractions was repurified on a 100 g SiO2 flash column with a gradient of MeOH/CH2Cl2 (1%, 2%, 3%) to obtain the desired compound as an oil (0.515 g, 0.00165 mol, 54%): 1H NMR (CDCl3) δ 0.97 (dd, J1 =9 Hz, J2 =6.9 Hz, 6H), 1.33 (d, J=6.9 Hz, 6H), 2.11-2.23 (m, 1H), 2.98 (s, 3H), 3.00-3.13 (m, 1H), 3.77 (s, 3H), 4.23-4.36 (m, 2H), 4.36-4.42 (m, 1H), 5.79-5.86 (br d, 1H), 7.46 (s, 1H). Mass spectrum: (M+H)+ =312.

Workup

  1. customSolvent was removed by rotary evaporation in vacuo
  2. customthe resulting oil dried on high vacuum for 1 hr
  3. washeluted with 20% EtOAc/CH2Cl2 and 3% MeOH/CH2Cl2
  4. customThe material obtained after concentration of the product fractions
  5. customwas repurified on a 100 g SiO2 flash column with a gradient of MeOH/CH2Cl2 (1%, 2%, 3%)

Sources & evidence

ORD record
ord-2559967320b744e6a7c316a19f34c064
Source dataset
uspto-grants-2000_11
Patent number
US06150530

Reaction notes

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