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Water → (R)-3-(6-Cyano-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester

HRID 2175193
ノート
印刷プレビュー

反応式

HRID 2175193 の反応式
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([NH:13][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[C:16](Cl)[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].O.CCOC(C)=O.[CH3:32][N:33](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([NH:13][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[C:16]([C:32]#[N:33])[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=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

7

反応物 4

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 58497459(R)-3-(6-Chloro-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester

生成物 1

HCID 58497401(R)-3-(6-Cyano-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester収率 96%

試薬・触媒・溶媒 2

HCID 11186
Zinc cyanide (Zn(CN)2)
触媒
HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
120 °C

実験手順

In a microwave reaction vessel was dissolved (R)-3-(6-chloro-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester (0.75 g, 2.14 mmol) in DMF (12 ml). Added the zinc cyanide (0.15 g, 1.29 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.25 g, 0.21 mmol). Reaction mixture was degassed using a stream of nitrogen and capped. Reaction was heated in a microwave at 120° C. for 1 hour and then stirred at room temperature for 72 hours. After this time the reaction was poured into water and EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc (3×). The combined organics were dried (MgSO4), filtered and concentrated to give the crude product which was purified via silica gel flash column chromatography (12 g silica gel, 5-20% EtOAc/hexanes) to afford 0.70 g (96%) of the title compound.

後処理

  1. customIn a microwave reaction vessel
  2. customReaction mixture
  3. customwas degassed
  4. customcapped
  5. customReaction
  6. customThe layers were separated
  7. extractionthe aqueous phase was extracted with EtOAc (3×)
  8. dry with materialThe combined organics were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give the crude product which
  12. customwas purified via silica gel flash column chromatography (12 g silica gel, 5-20% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-57ff62f288d54a7185bfce06271e99f0
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09062056B2

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