Water → HCID 11559737, compound

HRID 1092288Notes

Reaction equation

HRID 1092288 reaction equation
[OH-].[Li+].[CH3:3][N:4]([C:13]1[CH:14]=[C:15]([C:19]2[CH:20]=[N:21][C:22]([CH2:25][CH2:26][C:27]([O:29]C)=[O:28])=[N:23][CH:24]=2)[CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:6].O>O1CCCC1>[CH3:3][N:4]([C:13]1[CH:14]=[C:15]([C:19]2[CH:20]=[N:21][C:22]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[N:23][CH:24]=2)[CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 66591076HCID 66591076, compound

Product 1

HCID 11559737HCID 11559737, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.44 ml (1.45 mmol, 5 eq) of lithium hydroxide are added to a solution of 111 mg (0.29 mmol, 1 eq) of methyl 3-{5-[3-(1-methyl-3-pentylureido)phenyl]pyrimidin-2-yl}propanoate in 3 mL of tetrahydrofuran. The reaction mixture is stirred for four hours at room temperature. The reaction is stopped by adding 10 ml of water, washed with ether and then acidified with 1 N hydrochloric acid solution, and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then crystallized from ether. 66.7 mg of 3-{5-[3-(1-methyl-3-pentylureido)phenyl]pyrimidin-2-yl}propanoic acid are obtained in the form of white crystals. Yield=48%.

Workup

  1. washwashed with ether
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customThe solvents are evaporated off
  5. customthe residue is then crystallized from ether

Sources & evidence

ORD record
ord-fb0b9c97ae6d4169a6b9f0998df68f44
Source dataset
uspto-grants-2012_03
Patent number
US08129416B2

Reaction notes

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