Lithium Hydroxide → HCID 178490381, compound

HRID 333410Notes

Reaction equation

HRID 333410 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][NH:8][C:9](=[O:25])[NH:10][C@@H:11]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C:12]([O:14]C)=[O:13])[N:3]=[CH:2]1.[OH-].[Li+].O1CCCC1>O>[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][NH:8][C:9](=[O:25])[NH:10][CH:11]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[C:12]([OH:14])=[O:13])[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 178501384HCID 178501384, compound

Product 1

HCID 178490381HCID 178490381, compoundYield 570.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 500 mg (1.44 mmol) of methyl(S)-2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propanoate are added 500 mg of lithium hydroxide, 7 mL of tetrahydrofuran and 2 mL of water. The reaction medium is placed in a microwave reactor with stirring, at 100° C. for 10 minutes. Seven other identical tests are performed. The various tests are combined and concentrated to dryness. The crude product obtained is purified by filtration on a pad of silica (eluent: 1/1 dichloromethane/methanol). 2.73 g of 2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propanoic acid in the form of a pale yellow powder are obtained in a yield of 70%.

Workup

  1. customThe reaction medium is placed in a microwave reactor
  2. concentrationconcentrated to dryness
  3. customThe crude product obtained
  4. filtrationis purified by filtration on a pad of silica (eluent: 1/1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-0ef4102840a1444aaea132167d695aed
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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