Pyridine → tert-Butyl 2-[3-(aminocarbonylmethyl)phenoxy]-2-methylpropionate

HRID 480709ノート

反応式

HRID 480709 の反応式
[C:1]([O:5][C:6]([C:8]([CH3:21])([O:10][C:11]1[CH:12]=[C:13]([CH2:17][C:18](O)=[O:19])[CH:14]=[CH:15][CH:16]=1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:22]1C=CC=CC=1.C(=O)([O-])O.[NH4+].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>C(#N)C>[NH2:22][C:18]([CH2:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][C:8]([CH3:21])([CH3:9])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:19]

参加物

6

反応物 4

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonateHCID 187664143-(1-tert-Butoxycarbonyl-1-methylethoxy)phenylacetic Acid

生成物 1

HCID 18766448tert-Butyl 2-[3-(aminocarbonylmethyl)phenoxy]-2-methylpropionate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

3-(1-tert-Butoxycarbonyl-1-methylethoxy)phenylacetic acid (2.0 g, 6.79 mmol) is dissolved in acetonitrile (15 mL). Subsequently, pyridine (0.34 mL, 4.22 mmol) and ammonium hydrogencarbonate (699 mg, 8.84 mmol) were added thereto, and the mixture was stirred for 10 minutes at room temperature. Thereafter, di-tert-butyl dicarbonate [Boc2O (2.03 mL, 8.84 mmol)] was added thereto, and the resultant mixture was stirred for 14 hours. The reaction mixture was concentrated under reduced pressure. Thereafter, the resultant concentrate was added to water, and the mixture was extracted with chloroform, followed by washing sequentially with 1M hydrochloric acid and saturated brine. The resultant mixture was subjected to drying over magnesium sulfate, concentration under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol=10/1), whereby the target compound was obtained (1.07 g, 3.65 mmol, 53.6%).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationThereafter, the resultant concentrate
  3. additionwas added to water
  4. extractionthe mixture was extracted with chloroform
  5. washby washing sequentially with 1M hydrochloric acid and saturated brine
  6. dry with materialto drying over magnesium sulfate, concentration under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol=10/1), whereby the target compound
  7. customwas obtained (1.07 g, 3.65 mmol, 53.6%)

出典と根拠

ORDレコード
ord-3b4e6c4b8375471aabb9d7fc6c585f65
出典データセット
uspto-grants-2003_11
特許番号
US06653334B1

反応ノート

読み込み中…