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Thioglycolic Acid → methyl 3-{4-[(4-{[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]methoxy}benzyl)amino]phenyl}propanoate

HRID 508040
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HRID 508040 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[CH2:14][O:15][C:16]2[CH:47]=[CH:46][C:19]([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:18][CH:17]=2)=[CH:4][CH:3]=1.SCC(O)=O.O.[OH-].[Li+].C(=O)([O-])O.[Na+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2[CH2:14][O:15][C:16]2[CH:47]=[CH:46][C:19]([CH2:20][NH:21][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:18][CH:17]=2)=[CH:6][CH:7]=1
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참가 물질

6

반응물 4

HCID 1133Thioglycolic AcidHCID 168937Lithium hydroxide, monohydrateHCID 516892Sodium BicarbonateHCID 23157545methyl 3-(4-{(4-{[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]methoxy}benzyl)[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

생성물 1

HCID 23157576methyl 3-{4-[(4-{[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]methoxy}benzyl)amino]phenyl}propanoate
수율 66%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of the yellow oil obtained in Example 45 and mercaptoacetic acid (100 mg, 1.1 mmol) in N,N-dimethylformamide (5 mL) was added lithium hydroxide monohydrate (80 mg, 1.9 mmol), and the mixture was stirred at room temperature for 14 hr. The reaction mixture was poured into 10% aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated. The residue was purified by silica gel column chromatography (10%-80% ethyl acetate/hexane) to give the title compound (155 mg, yield 66%, 2 steps) as a yellow oil.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (10%-80% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-0cdb9f40abd24906b407f8665a649809
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07786165B2

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