Hydrochloric Acid → HCID 69421814, compound

HRID 350092Notes

Reaction equation

HRID 350092 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([O:28][CH2:29][C:30]2[N:31]=[C:32]([C:35]3[CH:40]=[N:39][CH:38]=[CH:37][N:36]=3)[S:33][CH:34]=2)[CH:27]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])=[CH:8]1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([O:28][CH2:29][C:30]2[N:31]=[C:32]([C:35]3[CH:40]=[N:39][CH:38]=[CH:37][N:36]=3)[S:33][CH:34]=2)[CH:27]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:9]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69420309HCID 69420309, compound

Product 1

HCID 69421814HCID 69421814, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-[1-[3-methoxy-5-[2-(2-pyrazinyl)-4-thiazolylmethoxy]benzyl]-4-phenyl-3-pyrrolyl]propionate (361 mg), 1N aqueous sodium hydroxide solution (1.5 ml), tetrahydrofuran (3 ml), and ethanol (3 ml) was stirred at room temperature for 4 hours, and 1N hydrochloric acid (1.5 ml) was added to the mixture, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The colorless crystals obtained were collected by filtration to yield 3-[1-[3-methoxy-5-[2-(2-pyrazinyl)-4-thiazolylmethoxy]benzyl]-4-phenyl-3-pyrrolyl]propionic acid (338 mg, yield: 99%). This was recrystallized from ethanol-hexane. Melting point: 111–112° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe colorless crystals obtained
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-c56478878fa2451b94a61ad60450b352
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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