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 235514Notes

Reaction equation

HRID 235514 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) 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.

Sources & evidence

ORD record
ord-e8e2be0e45d5406596bf48cecc641d78
Source dataset
uspto-grants-1997_01
Patent number
US05597926

Reaction notes

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