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

HRID 420587
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HRID 420587 반응식
[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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-ba410170e98e4c4abc4d5bc0b4e80f60
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08097610B2

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