Thioglycolic Acid → Methyl 3-[4-({[4'-(2-ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)phenyl]propanoate

HRID 508031Notes

Reaction equation

HRID 508031 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([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:15]=2)=[C:9]([CH3:46])[CH:8]=1)[CH3:2].SCC(O)=O.O.[OH-].[Li+].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]3[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:27]=3)[CH:15]=2)=[C:9]([CH3:46])[CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 1133Thioglycolic AcidHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 23157381Methyl 3-(4-{{[4'-(2-ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

Product 1

HCID 23157366Methyl 3-[4-({[4'-(2-ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)phenyl]propanoateYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the residue obtained in Example 34 and mercaptoacetic acid (0.278 mL, 4.00 mmol) in N,N-dimethylformamide (2 mL) was added lithium hydroxide monohydrate (0.336 g, 8.00 mmol), and the mixture was stirred at room temperature for 67 hr. Ethyl acetate was added to the residue, and the mixture was washed with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10%-40% ethyl acetate/hexane) to give the title compound (0.760 g, yield 82%, 2 steps) as a yellow oil.

Workup

  1. washthe mixture was washed with saturated aqueous sodium hydrogencarbonate and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (10%-40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-452b0c1d5a51441cab7a663789a147a6
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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