Potassium Carbonate → 4-{[(2,4-Dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-2-(4-phenoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 642334노트

반응식

HRID 642334 반응식
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:24]Br)=[O:5])[CH3:2].[CH2:26]([O:28][C:29](=[O:43])[CH2:30][NH:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=1[O:41][CH3:42])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:24][N:31]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=1[O:41][CH3:42])[CH2:30][C:29]([O:28][CH2:26][CH3:27])=[O:43])=[O:5])[CH3:2]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 19895532Ethyl 2-(2,4-dimethoxybenzylamino)acetateHCID 68428209HCID 68428209, 화합물

생성물 1

HCID 684286104-{[(2,4-Dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-2-(4-phenoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester수율 75.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-bromomethyl-2-(4-phenoxy-phenyl)-thiazole-5-carboxylic acid ethyl ester (1.12 g, 2.68 mmole), (2,4-dimethoxy-benzylamino)-acetic acid ethyl ester (737 mg, 2.90 mmole) and potassium carbonate (555 mg, 4.03 mmole) in anhydrous dimethylformamide (8 ml) was stirred at room temperature for 20 h before it was quenched with water, extracted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes to give the title compound as a yellow oil (1.20 g). MS: (+) m/z 613.07 (M+Na+).

후처리

  1. customwas quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and hexanes

출처 및 근거

ORD 기록
ord-e9df3eb3eb2142d196f51bc3a47df335
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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