Lithium Hydroxide → (S)-2-(2-benzoylphenylamino)-3-(3'-methylaminobiphenyl-4-yl)propionic acid

HRID 271848Notes

Reaction equation

HRID 271848 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C@@H:16]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([N:33](C)[C:34](NCCCCCCC)=O)[CH:28]=2)=[CH:23][CH:22]=1)[C:17]([OH:19])=[O:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1C=CC=CC=1N[C@@H](CC1C=CC(C2C=CC=C(NC)C=2)=CC=1)C(OCC)=O)(=O)C1C=CC=CC=1.[OH-].[Li+]>>[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C@@H:16]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][CH3:34])[CH:28]=2)=[CH:25][CH:26]=1)[C:17]([OH:19])=[O:18])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 10483579(S)-2-(2-benzoylphenylamino)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl)propionic acidHCID 69685584ethyl (S)-2-(2-benzoylphenylamino)-3-(3'-methylaminobiphenyl-4-yl)propionate

Product 1

HCID 68416880(S)-2-(2-benzoylphenylamino)-3-(3'-methylaminobiphenyl-4-yl)propionic acidYield 80%

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 1.2 g (1.06 mmol) of ethyl (S)-2-(2-benzoylphenyl-amino)-3-(3′-methylaminobiphenyl-4-yl)propionate (Example 1g) and 120 mg (2.85 mmol) of lithium hydroxide, 0.90 g of acid is obtained with an 80% yield.

Sources & evidence

ORD record
ord-6757a35a2e384da8b539ae92147ece0e
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Reaction notes

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