Sodium Hydroxide → 3-[3'-(1-Methyl-3-pentylureido)-2-pentyloxybiphenyl-4-yl]propanoic acid

HRID 250912Notes

Reaction equation

HRID 250912 reaction equation
[OH-].[Na+].[CH3:3][N:4]([C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([O:29]C)=[O:28])=[CH:21][C:20]=2[O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:6]>O1CCCC1.CO>[CH3:3][N:4]([C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:21][C:20]=2[O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67272943Methyl 3-[3'-(1-methyl-3-pentylureido)-2-pentyloxybiphenyl-4-yl]propanoate

Product 1

HCID 116554073-[3'-(1-Methyl-3-pentylureido)-2-pentyloxybiphenyl-4-yl]propanoic acidYield 74%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

In a manner similar to that of Example (19g), by reaction of 400 mg (10 mmol, 10 eq) of sodium hydroxide and methyl 3-[3′-(1-methyl-3-pentylureido)-2-pentyloxybiphenyl-4-yl]propanoate, obtained in the preceding step, in 10 ml of a tetrahydrofuran/methanol mixture (8/2), and after crystallization from pentane, 312 mg of 3-[3′-(1-methyl-3-pentylureido)-2-pentyloxybiphenyl-4-yl]propanoic acid are obtained in the form of a white powder (m.p.=83° C.). Yield=74% over the two steps.

Workup

  1. customafter crystallization from pentane, 312 mg of 3-[3′-(1-methyl-3-pentylureido)-2-pentyloxybiphenyl-4-yl]propanoic acid

Sources & evidence

ORD record
ord-e50b555aa9f942688556225530229b88
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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