Lithium Hydroxide → (S)-2-(2-benzoylphenylamino)-3-[3'-(1-methyl-3-naphthalen-2-ylureido)biphenyl-4-yl]propionic acid

HRID 271847Notes

Reaction equation

HRID 271847 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]([CH3:93])[C:80]([NH:82][C:83]3[CH:92]=[CH:91][C:90]4[C:85](=[CH:86][CH:87]=[CH:88][CH:89]=4)[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]([CH3:93])[C:80]([NH:82][C:83]3[CH:92]=[CH:91][C:90]4[C:85](=[CH:86][CH:87]=[CH:88][CH:89]=4)[CH:84]=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 10483579(S)-2-(2-benzoylphenylamino)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl)propionic acidHCID 86601618ethyl (S)-2-(2-benzoylphenylamino)-3-[3'-(1-methyl-3-naphthalen-2-ylureido)biphenyl-4-yl]propionate

Product 1

HCID 9809220(S)-2-(2-benzoylphenylamino)-3-[3'-(1-methyl-3-naphthalen-2-ylureido)biphenyl-4-yl]propionic acidYield 96.5%

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 0.66 g (1.02 mmol) of ethyl (S)-2-(2-benzoylphenylamino)-3-[3′-(1-methyl-3-naphthalen-2-ylureido)biphenyl-4-yl]propionate and 50 mg (1.19 mmol) of lithium hydroxide, 0.61 g of (S)-2-(2-benzoylphenylamino)-3-[3′-(1-methyl-3-naphthalen-2-ylureido)biphenyl-4-yl]propionic acid is obtained with a 96% yield. Melting point: 125° C.

Sources & evidence

ORD record
ord-7b54e74b86a247a5a3f03d8d496a228e
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Reaction notes

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