Lithium Hydroxide → HCID 11501851, compound

HRID 250927Notes

Reaction equation

HRID 250927 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]([O:12]C)=[O:11])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N:20]([CH3:29])[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:22])[CH:15]=1.[OH-].[Li+]>O1CCCC1>[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N:20]([CH3:29])[C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:22])[CH:15]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67273349HCID 67273349, compound

Product 1

HCID 11501851HCID 11501851, compoundYield 253.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 123.9 mg (0.311 mmol, 1 eq) of methyl 3-[2-amino-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate in 3 ml of tetrahydrofuran in the presence of 550 μL (0.623 mmol, 2 eq) of 1N lithium hydroxide solution is stirred at room temperature for 4 hours. The reaction medium is concentrated, hydrolyzed with water, acidified with acetic acid and extracted with ethyl acetate. The organic phase is dried over sodium sulfate and evaporated. The residue is taken up in heptane and then recrystallized from acetonitrile. 302.8 mg of 3-[2-amino-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoic acid are obtained in the form of a white powder (m.p.=84.9° C.) Yield=75%

Workup

  1. concentrationThe reaction medium is concentrated, hydrolyzed with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-5ffd736e4a434ddfb518bfc1eeab7af2
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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