Sodium Bicarbonate → Ethyl 2-{[(1-carbamoyl-1,2-dimethylpropyl)amino]methyl}-5-ethylnicotinate

HRID 1032820

反応式

HRID 1032820 の反応式
Cl[CH2:2][C:3]1[N:13]=[CH:12][C:11]([CH2:14][CH3:15])=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:16][C@@:17]([C:22]([NH2:24])=[O:23])([CH:19]([CH3:21])[CH3:20])[NH2:18].C(=O)(O)[O-].[Na+]>CS(C)=O>[C:22]([C:17]([NH:18][CH2:2][C:3]1[N:13]=[CH:12][C:11]([CH2:14][CH3:15])=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6])([CH3:16])[CH:19]([CH3:21])[CH3:20])(=[O:23])[NH2:24]

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 10154071(S)-2-Amino-2,3-dimethylbutanamideHCID 14600680Ethyl 2-chloromethyl-5-ethylnicotinate

生成物 1

HCID 14600682Ethyl 2-{[(1-carbamoyl-1,2-dimethylpropyl)amino]methyl}-5-ethylnicotinate

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A mixture of 77 g of ethyl 2-chloromethyl-5-ethylnicotinate (0.338 mol), 44 g of α-methylvalinamide (0.338 mol) and 33.5 g of sodium bicarbonate (0.4 mol) in 60 mL dimethylsulfoxide is stirred and heated at 80° for 16 hours. The reaction is partitioned between 1:1 ethylacetate-hexane and water. The organic layer is washed thoroughly with water, dried, and concentrated in vacuo to a gum. Chromatography of this gum on silica gel using hexane-ethyl acetate mixtures as eluant affords the title product, mp 68°-72°.

後処理

  1. temperatureheated at 80° for 16 hours
  2. customThe reaction is partitioned between 1:1 ethylacetate-hexane and water
  3. washThe organic layer is washed thoroughly with water
  4. customdried
  5. concentrationconcentrated in vacuo to a gum

出典と根拠

ORDレコード
ord-c574216ba4314168a9c07f2d176c404d
出典データセット
uspto-grants-1990_09
特許番号
US04959476

関連ノート

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