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 53930ノート

反応式

HRID 53930 の反応式
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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-770818230dc54aebbe42d3d0624d709d
出典データセット
uspto-grants-1997_04
特許番号
US05621109

反応ノート

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