Lithium Hydroxide → (S)-2-(2-{3'-[(benzoylmethylamino)methyl]biphenyl-4-yl}-1-carboxyethylamino)benzoic acid

HRID 1157492Notes

Reaction equation

HRID 1157492 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:86]=[CH:85][CH:84]=[CH:83][C:77]=3[C:78]([O:80]CC)=[O:79])[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(N(CC1C=C(C2C=CC(C[C@H](NC3C=CC=CC=3C(O)=O)C(O)=O)=CC=2)C=CC=1)C)(=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:86]=[CH:85][CH:84]=[CH:83][C:77]=3[C:78]([OH:80])=[O:79])[C:70]([OH:72])=[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

Participants

5

Reactant 4

HCID 3939Lithium HydroxideHCID 10346169(S)-2-(2-{3'-[(benzoyl methylamino)methyl]biphenyl-4-yl}-1-carboxyethylamino)-benzoic acidHCID 10483579(S)-2-(2-benzoylphenylamino)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl)propionic acidHCID 69685636ethyl (S)-2-(2-{3'-[(benzoylmethylamino)methyl]biphenyl-4-yl}-1-ethoxycarbonylethylamino)-benzoate

Product 1

HCID 68643282(S)-2-(2-{3'-[(benzoylmethylamino)methyl]biphenyl-4-yl}-1-carboxyethylamino)benzoic acidYield 74%

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 300 mg (0.53 mmol) of ethyl (S)-2-(2-{3′-[(benzoyl-methylamino)methyl]biphenyl-4-yl}-1-ethoxycarbonylethylamino)benzoate (Example 32) and 300 mg (7.14 mmol) of lithium hydroxide, 200 mg of (S)-2-(2-{3′-[(benzoyl methylamino)methyl]biphenyl-4-yl}-1-carboxyethylamino)-benzoic acid are obtained with a 74% yield.

Workup

  1. customare obtained with a 74% yield

Sources & evidence

ORD record
ord-a963cb02a6f5412a8d841dcd66b12a79
Source dataset
uspto-grants-2010_10
Patent number
US07807669B2

Reaction notes

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