Thioglycolic Acid → Methyl 3-[4-({[4'-(2-ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)phenyl]propanoate

HRID 508031노트

반응식

HRID 508031 반응식
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([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:15]=2)=[C:9]([CH3:46])[CH:8]=1)[CH3:2].SCC(O)=O.O.[OH-].[Li+].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]3[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:27]=3)[CH:15]=2)=[C:9]([CH3:46])[CH:8]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 1133Thioglycolic AcidHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 23157381Methyl 3-(4-{{[4'-(2-ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

생성물 1

HCID 23157366Methyl 3-[4-({[4'-(2-ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)phenyl]propanoate수율 82%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of the residue obtained in Example 34 and mercaptoacetic acid (0.278 mL, 4.00 mmol) in N,N-dimethylformamide (2 mL) was added lithium hydroxide monohydrate (0.336 g, 8.00 mmol), and the mixture was stirred at room temperature for 67 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 (10%-40% ethyl acetate/hexane) to give the title compound (0.760 g, yield 82%, 2 steps) as a yellow oil.

후처리

  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 (10%-40% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-452b0c1d5a51441cab7a663789a147a6
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786165B2

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