Methyl valinate hydrochloride → Methyl 3-methyl-2-(5-(4-nitrophenyl)oxazole-2-carboxamido)butanoate
반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([C:15]([O:17]CC)=O)=[N:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[CH3:21][O:22][C:23](=[O:29])[C@H:24]([CH:26]([CH3:28])[CH3:27])[NH2:25]>CCN(CC)CC>[CH3:27][CH:26]([CH3:28])[CH:24]([NH:25][C:15]([C:13]1[O:14][C:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[CH:11][N:12]=1)=[O:17])[C:23]([O:22][CH3:21])=[O:29]참가 물질
4
반응 조건
- 온도
- 110 °C
실험 절차
An ethanolic solution of Ethyl 5-(4-nitrophenyl)oxazole-2-carboxylate (step D product, 3.4 g) and L-valine methyl ester hydrochloride (5.43 g) previously neutralized with Et3N (4.52 ml), was heated in a sealed tube at 110° C. for 2 days. EtOH was removed under reduced pressure and the crude material was chromatographed on silica gel in 1:9 EtOAc:Pet ether to get cream colored solid which was crystallized in EtOAc/pet ether to yield 700 mg (31%) of the title compound. 1HNMR (DMSO-d6, 300 MHz): δ 9.2 (d, 1H), 8.37 (d, 2H), 8.24 (s, 1H), 8.14 (d, 2H), 4.32 (m, 1H), 3.68 (s, 3H), 2.26 (m, 1H), 0.96 (t, 6H); MS (ES+): m/z 348 (M+1).