Chloroacetyl chloride → 4-(4-Methoxy-benzyl)-6-methyl-[1,4]oxazepan-3-one

HRID 515452ノート

反応式

HRID 515452 の反応式
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][NH:8][CH2:9][CH:10]([CH3:13])[CH2:11][OH:12])=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[CH2:24][C:25](Cl)=[O:26].[OH-].[K+]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:9][CH:10]([CH3:13])[CH2:11][O:12][CH2:24][C:25]2=[O:26])=[CH:14][CH:15]=1

参加物

6

反応物 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 615277123-(4-Methoxy-benzylamino)-2-methyl-propan-1-ol

生成物 1

HCID 667185484-(4-Methoxy-benzyl)-6-methyl-[1,4]oxazepan-3-one収率 88.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 3-(4-methoxy-benzylamino)-2-methyl-propan-1-ol (4.14 g, 19.8 mmol) in dichloromethane (60 ml) was added triethylamine (2.20 g, 21.8 mmol) and chloroacetyl chloride (2.46 g, 21.8 mmol) at 0° C. The mixture was stirred at 0° C. for one hour and partitioned between 0.5N—HCl and dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was dissolved into 2-propanol (66.7 ml), then potassium hydroxide (2.22 g, 39.6 mmol) was added at 0° C. The mixture was stirred for 16 hours and partitioned between saturated ammonium chloride aqueous solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=1/1 to 1/3) to afford 4-(4-methoxy-benzyl)-6-methyl-[1,4]oxazepan-3-one as white solid (4.35 g, 88%).

後処理

  1. custompartitioned between 0.5N—HCl and dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved into 2-propanol (66.7 ml)
  6. stirringThe mixture was stirred for 16 hours
  7. custompartitioned between saturated ammonium chloride aqueous solution and ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=1/1 to 1/3)

出典と根拠

ORDレコード
ord-87d1530e0b324c06b2149087b84c7854
出典データセット
uspto-grants-2015_08
特許番号
US09108957B2

反応ノート

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