Thioglycolic Acid → [3-[[1-(6-Chlorobenzothiazole-2-yl)pyrrolidine-3-ylamino]methyl]phenyl]acetic acid methyl ester

HRID 420587Notes

Reaction equation

HRID 420587 reaction equation
[CH3:1][O:2][C:3](=[O:40])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][N:12]([CH:25]2[CH2:29][CH2:28][N:27]([C:30]3[S:31][C:32]4[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:33]=4[N:34]=3)[CH2:26]2)S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH:6]=1.SCC(O)=O.C1CCN2C(=NCCC2)CC1.CN(C)C=O>O>[CH3:1][O:2][C:3](=[O:40])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH:12][CH:25]2[CH2:29][CH2:28][N:27]([C:30]3[S:31][C:32]4[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:33]=4[N:34]=3)[CH2:26]2)[CH:6]=1

Participants

6

Reactant 4

HCID 1133Thioglycolic AcidHCID 6228DimethylformamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57966444HCID 57966444, compound

Product 1

HCID 16117699[3-[[1-(6-Chlorobenzothiazole-2-yl)pyrrolidine-3-ylamino]methyl]phenyl]acetic acid methyl esterYield 71.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of [3-[[[1-(6-chlorobenzothiazole-2-yl)pyrrolidine-3-yl]-(2-nitrobenzensulphonyl)amino]methyl]phenyl]acetic acid methyl ester (412 mg), mercaptoacetic acid (95 mL), 1,8-diazabicyclo[5,4,0]-7-undecene (4 mL) and dimethylformamide (4 mL) was stirred at room temperature for 1 hour. To the reaction solution was added water and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (204 mg). Yield: 71%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-ba410170e98e4c4abc4d5bc0b4e80f60
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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