Thioglycolic Acid → methyl 3-{4-[(4-{[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]methoxy}benzyl)amino]phenyl}propanoate

HRID 508040Notes

Reaction equation

HRID 508040 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[CH2:14][O:15][C:16]2[CH:47]=[CH:46][C:19]([CH2:20][N:21](S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.SCC(O)=O.O.[OH-].[Li+].C(=O)([O-])O.[Na+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[CH2:14][O:15][C:16]2[CH:47]=[CH:46][C:19]([CH2:20][NH:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1133Thioglycolic AcidHCID 168937Lithium hydroxide, monohydrateHCID 516892Sodium BicarbonateHCID 23157545methyl 3-(4-{(4-{[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]methoxy}benzyl)[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

Product 1

HCID 23157576methyl 3-{4-[(4-{[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]methoxy}benzyl)amino]phenyl}propanoateYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the yellow oil obtained in Example 45 and mercaptoacetic acid (100 mg, 1.1 mmol) in N,N-dimethylformamide (5 mL) was added lithium hydroxide monohydrate (80 mg, 1.9 mmol), and the mixture was stirred at room temperature for 14 hr. The reaction mixture was poured into 10% aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated. The residue was purified by silica gel column chromatography (10%-80% ethyl acetate/hexane) to give the title compound (155 mg, yield 66%, 2 steps) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (10%-80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0cdb9f40abd24906b407f8665a649809
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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