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Triethylamine → 3-[1-(4-carbamoyl-2-methylphenyl)-5-(4-[1,2,3]triazol-1-yl-phenyl)-1H-pyrrol-2-yl]-propionic acid ethyl ester

HRID 2280290
ノート
印刷プレビュー

反応式

HRID 2280290 の反応式
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1[N:8]([C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][C:20]=2[CH3:28])[C:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)[CH3:2].C(N(CC)CC)C.S([NH:47][N:48]=[CH:49][CH:50](Cl)Cl)(C1C=CC(C)=CC=1)(=O)=O>CO.O>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1[N:8]([C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][C:20]=2[CH3:28])[C:9]([C:12]2[CH:13]=[CH:14][C:15]([N:18]3[CH:50]=[CH:49][N:48]=[N:47]3)=[CH:16][CH:17]=2)=[CH:10][CH:11]=1)[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 583056233-[5-(4-aminophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl]propanoic acid ethyl esterHCID 671758942,2-Dichloroacetaldehyde tosylhydrazone2 回

生成物 1

HCID 583057293-[1-(4-carbamoyl-2-methylphenyl)-5-(4-[1,2,3]triazol-1-yl-phenyl)-1H-pyrrol-2-yl]-propionic acid ethyl ester収率 51.2%

試薬・触媒・溶媒 2

HCID 887
Methanol
溶媒
2 回
HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

Under a nitrogen atmosphere, 3-[5-(4-aminophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl]-propionic acid ethyl ester (11A, see Scheme 11) (103 mg, 0.26 mmol) was dissolved in methanol (5 mL). Triethylamine (0.07 mL, 0.48 mmol) was added. The mixture was cooled to 0° C. 2,2-dichloroacetaldehyde tosylhydrazone (15A) (62 mg, 0.22 mmol), dissolved in methanol (1.5 mL) was added slowly. The reaction was stirred at 0° C. for 5 min, and then heated to 40° C. for 3 hrs, then cooled to room temperature for 16 hrs. 2,2-dichloroacetaldehyde tosylhydrazone (15A) (62 mg) was added and stirred an additional 4 hr. The reaction was diluted with water (5 mL) and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by preparative TLC plate (1500 microns, 10% IPA/CH2Cl2). The desired band (RF=0.3) was isolated and dried under high vacuum to yield 3-[1-(4-carbamoyl-2-methylphenyl)-5-(4-[1,2,3]triazol-1-yl-phenyl)-1H-pyrrol-2-yl]-propionic acid ethyl ester (15B) (50 mg, 43%, light tan powder).

後処理

  1. additionwas added slowly
  2. temperatureheated to 40° C. for 3 hrs
  3. temperaturecooled to room temperature for 16 hrs
  4. stirringstirred an additional 4 hr
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude material was purified by preparative TLC plate (1500 microns, 10% IPA/CH2Cl2)
  11. customThe desired band (RF=0.3) was isolated
  12. customdried under high vacuum

出典と根拠

ORDレコード
ord-2bb63213272046e68885b98d712a9f83
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09138427B2

反応ノート

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