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

HRID 508031ノート

反応式

HRID 508031 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-452b0c1d5a51441cab7a663789a147a6
出典データセット
uspto-grants-2010_08
特許番号
US07786165B2

反応ノート

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