Lithium Hydroxide → (S)-3-{3'-[(benzoylmethylamino)methyl]biphenyl-4-yl}-2-(2-benzoylphenylamino)propionic acid

HRID 271852Notes

Reaction equation

HRID 271852 reaction equation
C(C1C=CC=CC=1N[C@@H](CC1C=CC(C2C=CC=C(N(C)C(NCCCCCCC)=O)C=2)=CC=1)C(O)=O)(=O)C1C=CC=CC=1.[C:45]([CH2:53][NH:54][CH2:55][C:56]1[CH:57]=[C:58]([C:62]2[CH:67]=[CH:66][C:65]([CH2:68][C@H:69]([NH:75][C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][C:77]=3[C:82](=[O:89])[C:83]3[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=3)[C:70]([O:72]CC)=[O:71])=[CH:64][CH:63]=2)[CH:59]=[CH:60][CH:61]=1)(=[O:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[OH-].[Li+]>>[C:45]([CH2:53][NH:54][CH2:55][C:56]1[CH:57]=[C:58]([C:62]2[CH:67]=[CH:66][C:65]([CH2:68][C@H:69]([NH:75][C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][C:77]=3[C:82](=[O:89])[C:83]3[CH:84]=[CH:85][CH:86]=[CH:87][CH:88]=3)[C:70]([OH:72])=[O:71])=[CH:64][CH:63]=2)[CH:59]=[CH:60][CH:61]=1)(=[O:52])[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 10483579(S)-2-(2-benzoylphenylamino)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl)propionic acidHCID 68417853ethyl (S)-3-{3'-[(benzoylmethylamino)methyl]biphenyl-4-yl}-2-(2-benzoylphenylamino)-propionate

Product 1

HCID 68415973(S)-3-{3'-[(benzoylmethylamino)methyl]biphenyl-4-yl}-2-(2-benzoylphenylamino)propionic acidYield 75%

Procedure

In a manner similar to the preparation of the (S)-2-(2-benzoylphenylamino)-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propionic acid (Example 2), using 0.63 g (1.06 mmol) of ethyl (S)-3-{3′-[(benzoylmethylamino)methyl]biphenyl-4-yl}-2-(2-benzoylphenylamino)-propionate (Example 28g) and 55 mg (1.04 mmol) of lithium hydroxide, 0.45 g of (S)-3-{3′-[(benzoylmethylamino)methyl]biphenyl-4-yl}-2-(2-benzoylphenylamino)propionic acid is obtained with a 75% yield.

Sources & evidence

ORD record
ord-2e3d3183b1ba47f88267cd92f012b218
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Reaction notes

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