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

HRID 52839Notes

Reaction equation

HRID 52839 reaction equation
[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

Participants

4

Reactant 3

HCID 53566263-(Pyridin-2-yl)prop-2-enoic acidHCID 10573507(2S,3S,5S)-2-amino-5-(N((3-furyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexaneHCID 22867556HCID 22867556, compound

Product 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-hydroxyhexaneYield 96%

Procedure

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) δ 0.73 (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.

Sources & evidence

ORD record
ord-a81d157e07064858af0990ac95aa7bf2
Source dataset
uspto-grants-1997_04
Patent number
US05616714

Reaction notes

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