Hydrochloric Acid → HCID 69423809, compound

HRID 350096Notes

Reaction equation

HRID 350096 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:31]=[C:32]([O:34][CH2:35][C:36]2[N:37]=[C:38]([C:41]3[CH:46]=[N:45][CH:44]=[CH:43][N:42]=3)[S:39][CH:40]=2)[CH:33]=1)[CH2:12][N:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])=[CH:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:31]=[C:32]([O:34][CH2:35][C:36]2[N:37]=[C:38]([C:41]3[CH:46]=[N:45][CH:44]=[CH:43][N:42]=3)[S:39][CH:40]=2)[CH:33]=1)[CH2:12][N:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69448086HCID 69448086, compound

Product 1

HCID 69423809HCID 69423809, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-[1-[3-benzyloxy-5-[2-(2-pyrazinyl)-4-thiazolylmethoxy]benzyl]-4-pheny-3-pyrrolyl]propionate (347 mg), 1N aqueous sodium hydroxide solution (5 ml), tetrahydrofuran (5 ml), and ethanol (5 ml) was stirred overnight under reflux conditions, and then 1N hydrochloric acid (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-benzyloxy-5-[2-(2-pyrazinyl)-4-thiazolylmethoxy]benzyl]-4-phenyl-3-pyrrolyl]propionic acid (274 mg, yield: 83%). This was recrystallized from ethanol-hexane. Melting point: 109–110° 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-8c6bd38243244cdaaba61cf8a98c1f45
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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