Ethyl (4E)-5-(2-{(1R)-1-[(2R)-oxiran-2-yl methoxy]ethyl}phenyl)pent-4-enoate → Ethyl (4E)-5-{2-[(1R)-1-({(2R)-3-[(2R)-2-(3-fluoro-4-methylbenzyl)azetidin-1-yl]-2-hydroxypropyl}oxy)ethyl]phenyl}pent-4-enoate

HRID 1920789Notes

Reaction equation

HRID 1920789 reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][C@@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1/[CH:14]=[CH:15]/[CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:7].[F:23][C:24]1[CH:25]=[C:26]([CH:32]=[CH:33][C:34]=1[CH3:35])[CH2:27][C@@H:28]1[CH2:31][CH2:30][NH:29]1>>[F:23][C:24]1[CH:25]=[C:26]([CH:32]=[CH:33][C:34]=1[CH3:35])[CH2:27][C@@H:28]1[CH2:31][CH2:30][N:29]1[CH2:3][C@@H:2]([OH:1])[CH2:4][O:5][C@@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1/[CH:14]=[CH:15]/[CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:7]

Participants

3

Reactant 2

HCID 58572679Ethyl (4E)-5-(2-{(1R)-1-[(2R)-oxiran-2-yl methoxy]ethyl}phenyl)pent-4-enoateHCID 58580768(2R)-2-(3-fluoro-4-methylbenzyl)azetidine

Product 1

HCID 58581183Ethyl (4E)-5-{2-[(1R)-1-({(2R)-3-[(2R)-2-(3-fluoro-4-methylbenzyl)azetidin-1-yl]-2-hydroxypropyl}oxy)ethyl]phenyl}pent-4-enoateYield 46%

Procedure

By using ethyl (4E)-5-(2-{(1R)-1-[(2R)-oxiran-2-yl methoxy]ethyl}phenyl)pent-4-enoate which had been obtained in Example 13 (13a) and (2R)-2-(3-fluoro-4-methylbenzyl)azetidine which had been obtained in Example 14 (14e), the reaction was carried out in the same manner as the method described in Example 1 (1f) to give the title compound as a colorless oily substance (yield 46%).

Sources & evidence

ORD record
ord-a3eb6ba7374341fe909445bc6514fc60
Source dataset
uspto-grants-2012_05
Patent number
US08173631B2

Reaction notes

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