Hydrochloric Acid → HCID 18174747, compound

HRID 747427Notes

Reaction equation

HRID 747427 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:29]3[CH:33]=[CH:32][N:31]=[C:30]3[CH3:34])[O:11][C:12]=2[CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][CH2:24][C:25]([O:27]C)=[O:26])=[CH:4][CH:3]=1.O1CCCC1.[OH-].[Na+].Cl>O.C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:29]3[CH:33]=[CH:32][N:31]=[C:30]3[CH3:34])[O:11][C:12]=2[CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 18174760HCID 18174760, compound

Product 1

HCID 18174747HCID 18174747, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of methyl 3-[2-[3-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]propoxy]phenyl]propionate (400 mg), tetrahydrofuran (5 ml) and ethanol (5 ml) was added 5 ml of a 1 N aqueous solution of sodium hydroxide, and the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into water (100 ml), and the mixture was neutralized with 1 N hydrochloric acid. The resulting solid precipitate was filtered, washed with water and air-dried to give crude crystals of 3-[2-[3-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]propoxy]phenyl]propionic acid. Recrystallization from tetrahydrofuran-hexane gave colorless prisms (260 mg, 54%). Melting point 184-185° C.

Workup

  1. filtrationThe resulting solid precipitate was filtered
  2. washwashed with water
  3. customair-dried

Sources & evidence

ORD record
ord-22be9264ff8f4d7995f636e4e2c43ebd
Source dataset
uspto-grants-2008_07
Patent number
US07396848B1

Reaction notes

Loading…