1,2-Dichloroethane → Propanoylamino-5-bromo-1-(4-methoxybenzyl)-4-methyl-2-pyridone

HRID 1387299ノート

反応式

HRID 1387299 の反応式
[C:1](O)(=[O:4])[CH2:2][CH3:3].C1C=NC2N(O)N=NC=2C=1.[CH3:16][O:17][C:18]1[CH:34]=[CH:33][C:21]([CH2:22][N:23]2[CH:28]=[C:27]([Br:29])[C:26]([CH3:30])=[C:25]([NH2:31])[C:24]2=[O:32])=[CH:20][CH:19]=1.C(Cl)CCl>C(Cl)Cl.CN(C=O)C>[C:1]([NH:31][C:25]1[C:24](=[O:32])[N:23]([CH2:22][C:21]2[CH:33]=[CH:34][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[CH:28]=[C:27]([Br:29])[C:26]=1[CH3:30])(=[O:4])[CH2:2][CH3:3]

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 1032Propionic AcidHCID 181649HOAtHCID 217064931-(4-Methoxybenzyl)-5-bromo-4-methyl-3-amino-2-pyridone

生成物 1

HCID 86757221Propanoylamino-5-bromo-1-(4-methoxybenzyl)-4-methyl-2-pyridone収率 44.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-(S)-tbutoxycarbonylamino-3-[4′-(1″-tbutoxycarbonyl-1″-methyl)ethyl]benzene]propanoic acid (3.20 g, 7.88 mmol) in methylene chloride (20 ml,) and DMF (5 mL) at 0° C. were added HOAT (1.07 g) and 1-(4-methoxybenzyl)-5-bromo-4-methyl-3-amino-2-pyridone (2.80 g, 8.67 mmol). EDC (1.66 g) and TMP (1.04 mL) were added, and the mixture was stirred coming to rt overnight. The methylene chloride was evaporated and DMF (25 mL) was added. Additional EDC (0.80 ;), HOAT (0.50 g) and TMP (0.5 mL) were added. After 3 hours the mixture was diluted with ethyl acetate, and washed with 1N HCl, aqueous sodium bicarbonate and brine. The organic phase was dried (MgSO4), filtered and evaporated. Chromatography of the residue over silica gel (ethyl acetate/hexane 1/3) gave 1-[2′-(S)-tbutoxycarbonylamino-)′-[4″-(1′″-tbutoxycarbonyl-1′″-methyl)ethyl]benzene]propanoylamino-5-bromo-1-(4-methoxybenzyl)-4-methyl-2-pyridone (2.48 g, 3.49 mmol, 44%).

後処理

  1. customThe methylene chloride was evaporated
  2. additionDMF (25 mL) was added
  3. additionAdditional EDC (0.80 ;), HOAT (0.50 g) and TMP (0.5 mL) were added
  4. additionAfter 3 hours the mixture was diluted with ethyl acetate
  5. washwashed with 1N HCl, aqueous sodium bicarbonate and brine
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-dc1f145301f34aa897b699eee03ed9c5
出典データセット
uspto-grants-2001_07
特許番号
US06268365B1

反応ノート

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