Lithium Hydroxide → (S)-2-(2-benzoylphenylamino)-3-{3'-[3-(4-dimethylaminophenyl)-1-methylureido]biphenyl-4-yl}propionic acid

HRID 1157482Notes

Reaction equation

HRID 1157482 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]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[NH:59][C@@H:60]([CH2:66][C:67]1[CH:72]=[CH:71][C:70]([C:73]2[CH:78]=[CH:77][CH:76]=[C:75]([N:79]([CH3:92])[C:80]([NH:82][C:83]3[CH:88]=[CH:87][C:86]([N:89]([CH3:91])[CH3:90])=[CH:85][CH:84]=3)=[O:81])[CH:74]=2)=[CH:69][CH:68]=1)[C:61]([O:63]CC)=[O:62])(=[O:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[OH-].[Li+]>>[C:45]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[NH:59][C@@H:60]([CH2:66][C:67]1[CH:72]=[CH:71][C:70]([C:73]2[CH:78]=[CH:77][CH:76]=[C:75]([N:79]([CH3:92])[C:80]([NH:82][C:83]3[CH:84]=[CH:85][C:86]([N:89]([CH3:91])[CH3:90])=[CH:87][CH:88]=3)=[O:81])[CH:74]=2)=[CH:69][CH:68]=1)[C:61]([OH:63])=[O:62])(=[O:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 10054914ethyl (S)-2-(2-benzoylphenylamino)-3-{3'-[3-(4-dimethylaminophenyl)-1-methylureido]biphenyl-4-yl}propionateHCID 10483579(S)-2-(2-benzoylphenylamino)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl)propionic acid

Product 1

HCID 11758461(S)-2-(2-benzoylphenylamino)-3-{3'-[3-(4-dimethylaminophenyl)-1-methylureido]biphenyl-4-yl}propionic acidYield 89%

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 0.60 g (0.9 mmol) of ethyl (S)-2-(2-benzoylphenylamino)-3-{3′-[3-(4-dimethylaminophenyl)-1-methylureido]biphenyl-4-yl}propionate (Example 4) and 43 mg (1.02 mmol) of lithium hydroxide, 0.41 g of (S)-2-(2-benzoylphenylamino)-3-{3′-[3-(4-dimethylaminophenyl)-1-methylureido]biphenyl-4-yl}propionic acid is obtained with an 89% yield.

Sources & evidence

ORD record
ord-941bfe110dac418e968d1e54b6a91b30
Source dataset
uspto-grants-2010_10
Patent number
US07807669B2

Reaction notes

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