Hydrochloric Acid → HCID 68717522, compound

HRID 508099Notes

Reaction equation

HRID 508099 reaction equation
[CH2:1]([S:3]([CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:17]=2[CH2:18][CH2:19][CH:20]3[N:25](S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[C:26]2[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[C:28]([F:37])[CH:27]=2)=[C:11]([CH3:50])[CH:10]=1)(=[O:5])=[O:4])[CH3:2].SCC(O)=O.O.[OH-].[Li+].[ClH:59]>CN(C)C=O.O>[ClH:59].[CH2:1]([S:3]([CH2:6][CH2:7][O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:17]=2[CH2:18][CH2:19][CH:20]3[NH:25][C:26]2[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[C:28]([F:37])[CH:27]=2)=[C:11]([CH3:50])[CH:10]=1)(=[O:4])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1133Thioglycolic AcidHCID 168937Lithium hydroxide, monohydrateHCID 23157302HCID 23157302, compound

Product 1

HCID 68717522HCID 68717522, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-{(4-{4-[2-(ethylsulfonyl)ethoxy]-2,6-dimethylphenyl}-2,3-dihydro-1H-inden-1-yl)[(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoic acid (0.620 g, 0.856 mmol) and mercaptoacetic acid (0.181 mg, 1.97 mmol) in N,N-dimethylformamide (20 mL) was added lithium hydroxide monohydrate (0.143 g, 3.42 mmol), and the mixture was stirred at room temperature for 2.5 hr. The reaction mixture was diluted with water, neutralized with 1 N hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-25% ethyl acetate/hexane), and the obtained residue was dissolved in ethyl acetate (10 mL) and treated with 4 N hydrogen chloride/ethyl acetate solution (0.170 mL) to give the title compound as colorless crystals (0.127 g, yield 26%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract 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 (hexane-25% ethyl acetate/hexane)
  6. dissolutionthe obtained residue was dissolved in ethyl acetate (10 mL)
  7. additiontreated with 4 N hydrogen chloride/ethyl acetate solution (0.170 mL)

Sources & evidence

ORD record
ord-2f5058375ead425d9ea827369ec09cab
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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