Hydrochloric Acid → HCID 23157256, compound

HRID 508094Notes

Reaction equation

HRID 508094 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([CH2:20][C:21]3[S:22][CH:23]=[C:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:25]=3)[CH2:17][CH2:18][CH3:19])=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH2:32][CH2:33][C:34]([O:36]CC)=[O:35].O1CCCC1.O.[OH-].[Li+].Cl>C(O)C.O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH:16]([CH2:20][C:21]3[S:22][CH:23]=[C:24]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:25]=3)[CH2:17][CH2:18][CH3:19])=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[CH2:32][CH2:33][C:34]([OH:36])=[O:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 23157665HCID 23157665, compound

Product 1

HCID 23157256HCID 23157256, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-{2-fluoro-4-[(4-{1-[(4-phenyl-1,3-thiazol-2-yl)methyl]butyl}benzyl)amino]phenyl}propanoate (0.420 g, 0.790 mmol) in a mixture of ethanol (6 mL), tetrahydrofuran (12 mL) and water (6 mL) was added lithium hydroxide monohydrate (0.198 g, 4.74 mmol), and the mixture was stirred at room temperature for 2.5 hr. The reaction mixture was neutralized with 1 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (15%-60% ethyl acetate/hexane) to give the title compound (330 mg, yield 83%) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (15%-60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2d9da39de32e467cb620b37c50911576
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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