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

HRID 53929

反応式

HRID 53929 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-207d37dcc669495a829a5618e72d5a3f
出典データセット
uspto-grants-1997_04
特許番号
US05621109

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