Dimethyl Sulfoxide → trans-7-Chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetaldehyde

HRID 1419060

反応式

HRID 1419060 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[N:21]([CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:20](=[O:27])[C@@H:19]([CH2:28][CH2:29][OH:30])[O:18][C@H:17]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:37])[C:16]=2[CH:38]=1>ClCCl.O.C(N(CC)CC)C>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[N:21]([CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:20](=[O:27])[C@@H:19]([CH2:28][CH:29]=[O:30])[O:18][C@H:17]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[Cl:37])[C:16]=2[CH:38]=1

参加物

7

反応物 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 69945756trans-7-Chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-ethanol

生成物 1

HCID 86752223trans-7-Chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetaldehyde収率 64.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒4 回HCID 8471Triethylamine溶媒

実験手順

To 25 ml of dichloromethane solution containing 0.70 ml of oxalyl chloride was added 5 ml of dichloromethane solution containing 0.71 ml of dimethylsulfoxide at -78° C., followed by stirring for 5 minutes. To the solution was slowly added 10 ml of dichloromethane solution containing 1.69 g of trans-7-chloro-5-(2chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-ethanol obtained in Example 160, followed by stirring for 15 minutes at -78° C. To the reaction mixture was added 2.79 ml of triethylamine and the mixture was further stirred for one hour at 0° C. and for 1.5 hours at room temperature. After the addition of 100 ml of water, extraction was performed with 100 ml of dichloromethane. The dichloromethane layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure. The residue was purified by column chromatography using silica gel (eluent, hexane:ethyl acetate=1:1) to give 1.08 g of trans-7-chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetaldehyde as light-yellow crystals, m.p.173° to 176° C.

後処理

  1. stirringby stirring for 15 minutes at -78° C
  2. stirringthe mixture was further stirred for one hour at 0° C. and for 1.5 hours at room temperature
  3. washThe dichloromethane layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated off under reduced pressure
  6. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-9c80a69db457441ba5857635ad34c799
出典データセット
uspto-grants-1999_03
特許番号
US05885979

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