Water → HCID 19348805、化合物

HRID 1418141ノート

反応式

HRID 1418141 の反応式
Cl.[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][NH2:13])=[CH:8][C:7]=1[NH:14][C:15](=[O:33])[CH2:16][CH:17]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=1[O:31][CH3:32])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])([CH3:5])([CH3:4])[CH3:3].[O-:34][C:35]#[N:36].[K+].O.C(=O)([O-])O.[Na+]>C(O)(=O)C>[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:35]([NH2:36])=[O:34])=[CH:8][C:7]=1[NH:14][C:15](=[O:33])[CH2:16][CH:17]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=1[O:31][CH3:32])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])([CH3:3])([CH3:4])[CH3:5]

参加物

6

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 11378442Potassium cyanateHCID 19348562N-[2-t-butyl-5-(aminomethyl)phenyl]-3-(2,4-dimethoxyphenyl)octanamide hydrochloride

生成物 1

HCID 19348805HCID 19348805、化合物収率 60%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 450 mg (0.94 mmol) of N-[2-t-butyl-5-(aminomethyl)phenyl]-3-(2,4-dimethoxyphenyl)octanamide-hydrochloride (prepared as described in Preparation 26B), 203 mg (2.50 mmol) of potassium cyanate, 30 ml of water and 1 ml of acetic acid was heated under reflux for 2 hours. At the end of this time, the reaction mixture was neutralized by adding sodium hydrogencarbonate, after which the mixture was extracted with ethyl acetate. The extract was washed several times with water and once with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 37 g of silica gel using a 100:5 mixture of ethyl acetate and methanol as the eluent, to give a crystalline product. This product was recrystallized from a mixture of methylene chloride and hexane to give 273 mg of the title compound in a 60% yield, melting at 112°-113° C. (from methylene chloride-methanol). Nuclear Magnetic Resonance Spectrum (270MHz, CDCl3) δ ppm:

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. extractionafter which the mixture was extracted with ethyl acetate
  4. washThe extract was washed several times with water
  5. dry with materialonce with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customthe resulting residue was purified by column chromatography through 37 g of silica gel using
  8. additiona 100:5 mixture of ethyl acetate and methanol as the eluent
  9. customto give a crystalline product
  10. customThis product was recrystallized from a mixture of methylene chloride and hexane

出典と根拠

ORDレコード
ord-f6d8684a8beb4cb9add1095d48624e47
出典データセット
uspto-grants-1999_03
特許番号
US05880147

反応ノート

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