3-(Pyridin-2-yl)prop-2-enoic acid → (2S,3S,5S)-2-(N-(N-(2-(6-Methylpyridinyl)methoxycarbonyl)valinyl)amino)-5-(N-((3-furyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane

반응식

[NH2:1][C@H:2]([C@@H:10]([OH:30])[CH2:11][C@@H:12]([NH:20][C:21]([O:23][CH2:24]C1C=COC=1)=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.N1C=CC=C[C:32]=1/[CH:37]=[CH:38]/[C:39]([OH:41])=O.[CH3:42][C:43]1[N:48]=[C:47]([CH2:49][O:50][C:51]([NH:53][C@H:54]([C:58]([OH:60])=O)[CH:55]([CH3:57])[CH3:56])=[O:52])[CH:46]=[CH:45][CH:44]=1>>[CH3:42][C:43]1[CH:44]=[CH:45][CH:46]=[C:47]([CH2:49][O:50][C:51]([NH:53][C@H:54]([C:58]([NH:1][C@H:2]([C@@H:10]([OH:30])[CH2:11][C@H:12]([NH:20][C:21]([O:23][CH2:24][C:39]2[O:41][CH:32]=[CH:37][CH:38]=2)=[O:22])[CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:60])[CH:55]([CH3:56])[CH3:57])=[O:52])[N:48]=1

참가 물질

반응물 3

HCID 53566263-(Pyridin-2-yl)prop-2-enoic acid

HCID 10573507(2S,3S,5S)-2-amino-5-(N((3-furyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane

HCID 22867556HCID 22867556, 화합물

생성물 1

HCID 471608(2S,3S,5S)-2-(N-(N-(2-(6-Methylpyridinyl)methoxycarbonyl)valinyl)amino)-5-(N-((3-furyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane수율 96%

실험 절차

Using the procedure of Example 6I but replacing the resultant compound of Example 6H with (2S,3S,5S)-2-amino-5-(N-((3-furyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane and replacing trans-3-(pyridinyl)acrylic acid with the resultant compound of Example 288 provided 92.9 mg (96%) of the desired compound as a white solid. 1H NMR (CDCl3) δ0.73 (d, 3H), 0.87 (d, 3H), 1.64 (m, 2H), 2.13 (m, 1H), 2.50 (s, 3H), 2.76 (dd, 2H), 2.84 (d, 2H), 3.67 (m, 1H), 3.75 (m, 1H), 3.88 (m, 1H), 4.17 (m, 1H), 4.90 (s, 2H), 5.09 (br d, 1H), 5.15-5.22 (m, 3H), 6.31 (br d, 1H), 6.37 (s, 1H), 7.07-7.25 (m, 12H), 7.39 (m, 2H), 7.60 (t, 1H). Mass spectrum: (M+H)+ =657.