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Acrylamide → (2S)-N2-[(3S)-1-(aminocarbonylethyl)pyrrolidin-3-yl]-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide

HRID 412642
ノート
印刷プレビュー

反応式

HRID 412642 の反応式
[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[C:21]([NH:23][C@H:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)=[O:22]>C(OCC)C.O>[NH3:5].[NH2:5][C:1]([CH2:2][CH2:3][N:26]1[CH2:27][CH2:28][C@H:24]([NH:23][C:21]([C@@H:16]2[CH2:17][CH2:18][CH2:19][CH2:20][N:15]2[C:7]2[O:6][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=2)=[O:22])[CH2:25]1)=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 6579AcrylamideHCID 57068119(2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3S)-pyrrolidin-3-yl]-2-piperidinecarboxamide

生成物 2

HCID 222AmmoniaHCID 57170845(2S)-N2-[(3S)-1-(aminocarbonylethyl)pyrrolidin-3-yl]-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide収率 83.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 3283
Diethyl Ether
溶媒

実験手順

Acrylamide (11.6 mg) was added to a solution of (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3S)-pyrrolidin-3-yl]-2-piperidinecarboxamide (51.6 mg) [see Example 4] in diethyl ether (3 ml). The reaction mixture was refluxed for 18 hours, after which time the ethereal layer was diluted with water. The aqueous layer was separated and then extracted with ethyl acetate. The combined organic layers were dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 93:7:1, changing to 90:10:1, dichloromethane:methanol:0.88 aqueous ammonia solution to afford (2S)-N2-[(3S)-1-(aminocarbonylethyl)pyrrolidin-3-yl]-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide (26.4 mg) as an off-white foam.

後処理

  1. temperatureThe reaction mixture was refluxed for 18 hours
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulphate
  5. customthe solvent removed under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 93:7:1

出典と根拠

ORDレコード
ord-de57429a710849f19f7ee529482f6266
出典データセット
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06562964B1

反応ノート

読み込み中…

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