Benzoic acid, 2-mercapto-, methyl ester → (+/-)-3-Butyl-3-ethyl-2,3-dihydro-1,4-benzothiazepin-5(4H)-one

HRID 398819ノート

反応式

HRID 398819 の反応式
[C:1]([O:10]C)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[CH2:12]([C:16]1([CH2:19][CH3:20])[CH2:18][NH:17]1)[CH2:13][CH2:14][CH3:15]>CO>[CH2:12]([C:16]1([CH2:19][CH3:20])[NH:17][C:1](=[O:10])[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[S:4][CH2:18]1)[CH2:13][CH2:14][CH3:15]

参加物

4

反応物 2

HCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 217099702-Butyl-2-ethylaziridine

生成物 1

HCID 18968861(+/-)-3-Butyl-3-ethyl-2,3-dihydro-1,4-benzothiazepin-5(4H)-one収率 97.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of methyl thiosalicylate (25.0 g, Aldrich) in methanol (95 ml) at 0° C. was added 2-butyl-2-ethylaziridine (20.0 g, Synthetic Example 1(f)) and the mixture was stirred at room temperature for 18 hours. Solvent was evaporated and toluene (200 ml) and sodium methoxide (8.2 g) were added. The mixture was heated to reflux for 4.5 hours, removing water through a Dean-Stark trap. Solvent was evaporated and the residue was partitioned between 5% HCl (500 ml) and dichloromethane (400 ml). The organic layer was separated, dried and concentrated. Crystallization from hexanes/ethyl acetate provided the title compound as a white solid (38.0 g), mp 92°-93° C. 1H NMR consistent with the proposed structure.

後処理

  1. customSolvent was evaporated
  2. additiontoluene (200 ml) and sodium methoxide (8.2 g) were added
  3. temperatureThe mixture was heated
  4. temperatureto reflux for 4.5 hours
  5. customremoving water through a Dean-Stark trap
  6. customSolvent was evaporated
  7. customthe residue was partitioned between 5% HCl (500 ml) and dichloromethane (400 ml)
  8. customThe organic layer was separated
  9. customdried
  10. concentrationconcentrated
  11. customCrystallization from hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-82ff9468691442bb9de9ea51b9fb9413
出典データセット
uspto-grants-1998_10
特許番号
US05817652

反応ノート

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