Hydrochloric Acid → HCID 22261924, compound

HRID 1610581Notes

Reaction equation

HRID 1610581 reaction equation
[C:1]1([C:12]([NH:14][CH:15]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][C:39]([F:44])([F:43])[CH:40]([F:42])[F:41])[CH:33]=2)[CH:16]([C:18]2[CH:30]=[CH:29][C:21]([O:22][CH2:23][C:24]([O:26]CC)=[O:25])=[CH:20][CH:19]=2)[OH:17])=[O:13])[C:6]2[CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO>[C:1]1([C:12]([NH:14][CH:15]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][C:39]([F:43])([F:44])[CH:40]([F:41])[F:42])[CH:33]=2)[CH:16]([C:18]2[CH:30]=[CH:29][C:21]([O:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:20][CH:19]=2)[OH:17])=[O:13])[C:6]2[CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86593271HCID 86593271, compound

Product 1

HCID 22261924HCID 22261924, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (4-{(1RS,2SR)-2-[(6,7-dihydro-5H-benzo[a][7]annulen-1-ylcarbonyl)amino]-1-hydroxy-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]propyl}phenoxy)acetate (100 mg, 0.163 mmol) in methanol (20 ml) was added 2N aqueous sodium hydroxide solution (0.16 ml, 0.32 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was acidified with 1N hydrochloric acid and extracted with ethyl acetate (100 ml×2). The extract was washed with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-ethyl acetate-methanol=10:1). Recrystallization from ethyl acetate-hexane gave the objective substance (87 mg, 91%).

Workup

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-ethyl acetate-methanol=10:1)
  6. customRecrystallization from ethyl acetate-hexane
  7. customgave the objective substance (87 mg, 91%)

Sources & evidence

ORD record
ord-634caf8ea34d4b0093ec86e17b073bcd
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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