N,N-Bis(2-hydroxyethyl)-p-toluidine → (2S)-3-{3-bromo-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)-ethoxy]-phenyl}-2-(4-p-tolyl-piperazin-1-yl)-propionic acid

HRID 1984123Notes

Reaction equation

HRID 1984123 reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[C:9]([Br:28])[CH:8]=1)[C:3]([OH:5])=[O:4].[C:29]1([CH3:42])[CH:34]=[CH:33][C:32]([N:35]([CH2:39][CH2:40]O)[CH2:36][CH2:37]O)=[CH:31][CH:30]=1>>[Br:28][C:9]1[CH:8]=[C:7]([CH2:6][C@H:2]([N:1]2[CH2:40][CH2:39][N:35]([C:32]3[CH:31]=[CH:30][C:29]([CH3:42])=[CH:34][CH:33]=3)[CH2:36][CH2:37]2)[C:3]([OH:5])=[O:4])[CH:12]=[CH:11][C:10]=1[O:13][CH2:14][CH2:15][C:16]1[N:17]=[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:19][C:20]=1[CH3:21]

Participants

3

Reactant 2

HCID 76497N,N-Bis(2-hydroxyethyl)-p-toluidineHCID 69063835(2S)-2-amino-3-{3-bromo-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid

Product 1

HCID 11556228(2S)-3-{3-bromo-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)-ethoxy]-phenyl}-2-(4-p-tolyl-piperazin-1-yl)-propionic acidYield 24%

Procedure

Following the procedures described in Example 1, Intermediate 3B was used in place of Intermediate 3A, and 2,2′-(p-tolylazanediyl)diethanol was used in place of 2,2′-(m-tolylazanediyl)diethanol to give (2S)-3-{3-bromo-4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)-ethoxy]-phenyl}-2-(4-p-tolyl-piperazin-1-yl)-propionic acid as a white solid with the yield of 24% and mp of 203-205° C.

Sources & evidence

ORD record
ord-f6801502c89e483f84c48ba3e497310e
Source dataset
uspto-grants-2009_06
Patent number
US07544687B2

Reaction notes

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