Thioglycolic Acid → HCID 67327651, compound

HRID 1023347Notes

Reaction equation

HRID 1023347 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9](S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:10][CH2:11][C:12]2[CH:31]=[CH:30][C:15]([CH2:16][N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.SCC(O)=O.[Li+].[OH-]>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH2:10][CH2:11][C:12]2[CH:31]=[CH:30][C:15]([CH2:16][N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:19][CH2:18]3)=[CH:14][CH:13]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 1133Thioglycolic Acid2×HCID 3939Lithium Hydroxide2×HCID 70944787HCID 70944787, compound

Product 1

HCID 67327651HCID 67327651, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-[4-(2-{(4-methoxyphenyl)[(2-nitrophenyl)sulfonyl]-amino}ethyl)benzyl]piperazine-1-carboxylate in DMF (35 mL) was added mercaptoacetic acid (1.35 mL) and LiOH (1.63 g) at room temperature, then the reaction mixture was stirred over night. The reaction mixture was added mercaptoacetic acid (1.35 mL) and LiOH (1.63 g), and stirred for 5 hours. The reaction mixture was diluted with H2O, and extracted with AcOEt. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1 to 1/2) to afford tert-butyl 4-(4-{2-[(4-methoxyphenyl)amino]ethyl}benzyl)piperazine-1-carboxylate as a pale yellow amorphous (5.96 g).

Workup

  1. stirringstirred for 5 hours
  2. extractionextracted with AcOEt
  3. washThe organic layer was washed with water and saturated aqueous NaCl
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1 to 1/2)

Sources & evidence

ORD record
ord-2b68b5c3907b4802858b60f78893844e
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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