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

HRID 250902Notes

Reaction equation

HRID 250902 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[C:15]([CH2:17][CH2:18][C:19]([O:21]C)=[O:20])[CH:14]=[CH:13][C:12]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:40])[C:30]([NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:31])[CH:24]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1.CO>[CH2:3]([O:10][C:11]1[CH:16]=[C:15]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:14]=[CH:13][C:12]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([N:29]([CH3:40])[C:30]([NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:31])[CH:24]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67272651Methyl 3-[2-benzyloxy-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate

Product 1

HCID 116777753-[2-Benzyloxy-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acidYield 65%

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-benzyloxy-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-benzyloxy-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoic acid are obtained in the form of a white powder (m.p.=76° C.). Yield=65% over the two steps.

Workup

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

Sources & evidence

ORD record
ord-ad3a7fb0f74a41769a0cc6d07ae2a8de
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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