Allyl bromide → 2-Allyloxy-3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-propionic acid ethyl ester

HRID 47820Notes

Reaction equation

HRID 47820 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH:5]([OH:30])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:9][CH:8]=1)[CH3:2].[CH2:32](Br)[CH:33]=[CH2:34]>>[CH2:1]([O:3][C:4](=[O:31])[CH:5]([O:30][CH2:34][CH:33]=[CH2:32])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:9][CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 7841Allyl bromideHCID 698837723-{4-[2-(Tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-hydroxy-propionic acid ethyl ester

Product 1

HCID 698838562-Allyloxy-3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-propionic acid ethyl esterYield 41%

Procedure

Synthesized from 3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-hydroxy-propionic acid ethyl ester using a procedure analogous to that used for Example 47 and substituting allyl bromide as the electrophile to give 2-allyloxy-3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-propionic acid ethyl ester as a clear oil (187 mg, 41%)

Sources & evidence

ORD record
ord-42305015eedf4629bbcd6d46286687b4
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

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