Thioglycolic Acid → methyl 3-[4-({4-[(2-phenyl-1H-indol-1-yl)methyl]benzyl}amino)phenyl]propanoate

HRID 508027Notes

Reaction equation

HRID 508027 reaction equation
[N+](C1C=CC=CC=1S([N:13]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][N:34]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:36]=[C:35]2[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:29][CH:28]=1)[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=1)(=O)=O)([O-])=O.SCC(O)=O.O.[OH-].[Li+].C(OCC)(=O)C>CN(C)C=O>[C:43]1([C:35]2[N:34]([CH2:33][C:30]3[CH:29]=[CH:28][C:27]([CH2:26][NH:13][C:14]4[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:19]=4)=[CH:32][CH:31]=3)[C:42]3[C:37]([CH:36]=2)=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

6

Reactant 4

HCID 1133Thioglycolic AcidHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 23157671methyl 3-[4-([(2-nitrophenyl)sulfonyl]{4-[(2-phenyl-1H-indol-1-yl)methyl]benzyl}amino)phenyl]propanoate

Product 1

HCID 23157646methyl 3-[4-({4-[(2-phenyl-1H-indol-1-yl)methyl]benzyl}amino)phenyl]propanoateYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the residue obtained in Example 9 and mercaptoacetic acid (0.209 mL, 3.00 mmol) in N,N-dimethylformamide (2 mL) was added lithium hydroxide monohydrate (0.252 g, 6.00 mmol), and the mixture was stirred at room temperature for 64 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 (hexane-25% ethyl acetate/hexane) to give the title compound (0.470 g, yield 66%, 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 (hexane-25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d8a3c48219874bce859a0d22116473ef
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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