Sodium Hydroxide → 3-[2-(3-Fluorobenzyloxy)-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acid

HRID 250904Notes

Reaction equation

HRID 250904 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:39]=[CH:40][CH:41]=1)[CH2:7][O:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([O:19]C)=[O:18])[CH:12]=[CH:11][C:10]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N:27]([CH3:38])[C:28]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:29])[CH:22]=1>O1CCCC1.CO>[F:3][C:4]1[CH:5]=[C:6]([CH:39]=[CH:40][CH:41]=1)[CH2:7][O:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:12]=[CH:11][C:10]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N:27]([CH3:38])[C:28]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:29])[CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67272312Methyl 3-[2-(3-fluorobenzyloxy)-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate

Product 1

HCID 116133113-[2-(3-Fluorobenzyloxy)-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acidYield 68%

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-[2-(3-fluorobenzyloxy)-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate, obtained in the preceding step, in 10 ml of a tetrahydrofuran/methanol mixture (8/2), and after crystallization from pentane, 305 mg of 3-[2-(3-fluorobenzyloxy)-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acid are obtained in the form of a white powder (m.p.=73° C.). Yield=68% over the two steps.

Workup

  1. customafter crystallization from pentane, 305 mg of 3-[2-(3-fluorobenzyloxy)-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acid

Sources & evidence

ORD record
ord-dfee1df686b14eaeb0c1091430e0cb45
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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