Acetamidomalonic acid diethyl ester → Diethyl acetamido[(pyridin-4-yl)methyl]propanedioate

HRID 2230024ノート

反応式

HRID 2230024 の反応式
COC(=O)C([CH2:21][C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)NC(=O)CN(S(C1C=CC(C)=CC=1)(=O)=O)C.[Na].[C:30]([NH:33][CH:34]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:35]([O:37][CH2:38][CH3:39])=[O:36])(=[O:32])[CH3:31].Cl.N1C=CC(CCl)=CC=1>CCO>[N:25]1[CH:26]=[CH:27][C:22]([CH2:21][C:34]([NH:33][C:30](=[O:32])[CH3:31])([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:23][CH:24]=1

参加物

6

反応物 4

HCID 14041Acetamidomalonic acid diethyl esterHCID 745704-(Chloromethyl)pyridinium chlorideHCID 5360545SodiumHCID 18464215HCID 18464215、化合物

生成物 1

HCID 13817909Diethyl acetamido[(pyridin-4-yl)methyl]propanedioate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

N-(Toluene4-sulfonyl)sarcosyl-β-(pyrid-4-yl)-D,L-alanine methyl ester was employed in this reaction and was prepared as follows. Sodium metal (2 eq.) was dissolved in EtOH containing diethyl acetamidomalonate (1 eq.) and 4-picolylchloride hydrochloride (1 eq.). The mixture was heated to reflux for 6 hr, and then cooled and filtered to remove NaCl (washed with EtOH). The solvent was removed in vacuo and the mixture was taken up into saturated aq NaHCO3 and extracted with EtOAc. The solvent was removed and the residue purified by silica gel flash chromatography (95:5 CH2Cl2/MeOH) to give diethyl 2-(4-pyridylmethyl)-2-acetamidomalonate.

後処理

  1. customwas prepared
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 6 hr
  4. temperaturecooled
  5. filtrationfiltered
  6. customto remove NaCl (washed with EtOH)
  7. customThe solvent was removed in vacuo
  8. extractionextracted with EtOAc
  9. customThe solvent was removed
  10. customthe residue purified by silica gel flash chromatography (95:5 CH2Cl2/MeOH)

出典と根拠

ORDレコード
ord-2e0025cbd5dc4fbea6310f3358748bcd
出典データセット
uspto-grants-2002_07
特許番号
US06423688B1

反応ノート

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