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Tetrahydrofuran → Ethyl 2-(2-(tert-butoxycarbonylamino)pyridin-4-yl)propanoate

HRID 2069058
ノート
印刷プレビュー

反応式

HRID 2069058 の反応式
Cl[C:2]1[CH:7]=[C:6]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:4][N:3]=1.C([NH:19][C:20](=[O:22])[O-:21])(C)(C)C.[C:23](=O)([O-])[O-].[Cs+].[Cs+].[CH2:29]1[CH2:33]OC[CH2:30]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[C:29]([O:21][C:20]([NH:19][C:2]1[CH:7]=[C:6]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:4][N:3]=1)=[O:22])([CH3:30])([CH3:33])[CH3:23]
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

7

反応物 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 21252905Tert-butylcarbamateHCID 58532560Ethyl 2-(2-chloropyridin-4-yl)propanoate

生成物 1

HCID 58532575Ethyl 2-(2-(tert-butoxycarbonylamino)pyridin-4-yl)propanoate収率 61%

試薬・触媒・溶媒 2

HCID 636044
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
触媒
HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
65 °C

実験手順

A mixture of ethyl 2-(2-chloropyridin-4-yl)propanoate (51) (1.55 g, 7.25 mmol), tert-butylcarbamate (2.55 g, 21.76 mmol), Pd2 dba3 (0.166 g, 0.181 mmol), caesium carbonate (3.55 g, 10.88 mmol) and Xantphos (0.210 g, 0.363 mmol) in THF (10 mL) was purged with nitrogen and heated at 65° C. for 48 hr. The mixture was then cooled to RT, diluted with water and extracted with ether. The ether layer was washed with water and brine and then dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 100 g, 5-10% EtOAc in isohexane, gradient elution) to afford the title compound (52) (1.35 g, 61%): m/z 295 (M+H)+ (ES+).

後処理

  1. customwas purged with nitrogen
  2. temperatureThe mixture was then cooled to RT
  3. additiondiluted with water
  4. extractionextracted with ether
  5. washThe ether layer was washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by flash column chromatography (SiO2, 100 g, 5-10% EtOAc in isohexane, gradient elution)

出典と根拠

ORDレコード
ord-663ab8ce6d8147fdbdd8d3baf21496f6
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08299073B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート