Lithium Hydroxide → 2(S)-ethoxy-3-{4-[2-(1-methyl-3-pentylureido)thiazol-5-yl]phenyl}propanoic acid

HRID 910300Notes

Reaction equation

HRID 910300 reaction equation
[CH2:1]([O:3][C@@H:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[S:20][C:19]([N:21]([CH3:30])[C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:23])=[N:18][CH:17]=2)=[CH:12][CH:11]=1)[C:5]([O:7]C)=[O:6])[CH3:2].[OH-].[Li+]>>[CH2:1]([O:3][C@@H:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[S:20][C:19]([N:21]([CH3:30])[C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:23])=[N:18][CH:17]=2)=[CH:12][CH:11]=1)[C:5]([OH:7])=[O:6])[CH3:2]

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 67148249methyl 2(S)-ethoxy-3-{4-[2-(1-methyl-3-pentylureido)thiazol-5-yl]phenyl}propanoate

Product 1

HCID 671477352(S)-ethoxy-3-{4-[2-(1-methyl-3-pentylureido)thiazol-5-yl]phenyl}propanoic acidYield 86%

Procedure

In a manner similar to that of Example 7j, starting with 0.06 g (0.14 mmol) of methyl 2(S)-ethoxy-3-{4-[2-(1-methyl-3-pentylureido)thiazol-5-yl]phenyl}propanoate and 0.2 ml (0.2 mmol) of aqueous 1M lithium hydroxide solution, 0.05 g (86%) of 2(S)-ethoxy-3-{4-[2-(1-methyl-3-pentylureido)thiazol-5-yl]phenyl}propanoic acid is obtained in the form of a white solid with a melting point of 114° C.

Sources & evidence

ORD record
ord-c4d6d2a012be438a812e740136f32076
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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