Acetic Acid → HCID 178490376, compound

HRID 333444Notes

Reaction equation

HRID 333444 reaction equation
O.[OH-].[Li+].[NH:4]1[CH:8]=[C:7]([CH2:9][NH:10][C:11](=[O:27])[NH:12][C@@H:13]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:14]([O:16]C)=[O:15])[N:6]=[CH:5]1.C(O)(=O)C>O1CCCC1.O>[NH:4]1[CH:8]=[C:7]([CH2:9][NH:10][C:11](=[O:27])[NH:12][CH:13]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[C:14]([OH:16])=[O:15])[N:6]=[CH:5]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 168937Lithium hydroxide, monohydrateHCID 178501383methyl(S)-2-[3-(1H-imidazol-4-ylmethyl)ureido]-3-(4-methoxy-phenyl)propanoate

Product 1

HCID 178490376HCID 178490376, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

351 mg (84 mmol) of lithium hydroxide monohydrate are added to a solution of 278 mg (8.4 mmol) of methyl(S)-2-[3-(1H-imidazol-4-ylmethyl)ureido]-3-(4-methoxy-phenyl)propanoate in 5 mL of tetrahydrofuran and 1 mL of water. The reaction mixture is heated for 10 minutes at 100° C. in a microwave reactor. The reaction is stopped by adding 2 mL of water and 0.5 mL of acetic acid and is then extracted with ethyl acetate. The aqueous phase is concentrated to dryness and the residue is then chromatographed on silica gel (eluent: 7/3 dichloromethane/methanol). 261 mg of 2-[3-(1H-imidazol-4-ylmethyl)ureido]-3-(4-methoxyphenyl)propionic acid in the form of a white foam are obtained in a yield of 98%.

Workup

  1. extractionis then extracted with ethyl acetate
  2. concentrationThe aqueous phase is concentrated to dryness
  3. customthe residue is then chromatographed on silica gel (eluent: 7/3 dichloromethane/methanol)

Sources & evidence

ORD record
ord-3267ca5a71f6447a88b8937b95876a6f
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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