Water → 2-{[(1-Carbamoyl-1,2-dimethylpropyl)amino]methyl}-5-ethylnicotinic acid

HRID 1032821

反応式

HRID 1032821 の反応式
[C:1]([C:4]([NH:9][CH2:10][C:11]1[N:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][C:12]=1[C:13]([O:15]CC)=[O:14])([CH3:8])[CH:5]([CH3:7])[CH3:6])(=[O:3])[NH2:2].[OH-].[Na+].O>CO.C(OCC)(=O)C.O1CCCC1>[C:1]([C:4]([NH:9][CH2:10][C:11]1[N:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][C:12]=1[C:13]([OH:15])=[O:14])([CH3:8])[CH:5]([CH3:7])[CH3:6])(=[O:3])[NH2:2]

参加物

7

反応物 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 14600682Ethyl 2-{[(1-carbamoyl-1,2-dimethylpropyl)amino]methyl}-5-ethylnicotinate

生成物 1

HCID 146006872-{[(1-Carbamoyl-1,2-dimethylpropyl)amino]methyl}-5-ethylnicotinic acid収率 60.7%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 5.6 g of ethyl 2-{[(1-carbamoyl-1,2-dimethylpropyl)amino]methyl}-5-ethylnicotinate (0.0174 mol) in 30 mL of methanol containing 2 g of NaOH (0.05 mol) and 10 mL water is stirred at room temperature for two hours and 30 minutes. The reaction is concentrated in vacuo and redissolved in 30 mL water; adjustment of the pH to 4 with concentrated hydrochloric acid and concentration in vacuo gives a gum. This residue is dissolved in a mixture of ethyl acetate, tetrahydrofuran, and methanol, dried over MgSO4, and concentrated in vacuo to 6 g foam. Crystallization from methanol-ether affords 3.1 g product, mp 180°-181° C.

後処理

  1. concentrationThe reaction is concentrated in vacuo
  2. dissolutionredissolved in 30 mL water
  3. concentrationadjustment of the pH to 4 with concentrated hydrochloric acid and concentration in vacuo
  4. customgives a gum
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo to 6 g foam
  7. customCrystallization from methanol-ether

出典と根拠

ORDレコード
ord-9a7e116d702d4d9fa5d02fe8e88ad2d0
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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