Oxalyl chloride → HCID 10026851、化合物

HRID 1446424ノート

反応式

HRID 1446424 の反応式
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11]([OH:13])=O.C(Cl)(=O)C(Cl)=O.Cl.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[CH:29]([NH2:31])[CH3:30])=[CH:24][CH:23]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C)C=O>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH2:32][C:33]2[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=2)[CH:29]([NH:31][C:11]([CH:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1]2)=[O:13])[CH3:30])=[CH:24][CH:23]=1

参加物

7

反応物 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 1013701,2,3,4-Tetrahydro-2-naphthoic acidHCID 222704272,3-Bis(4-chlorophenyl)-1-methylpropylamine hydrochloride

生成物 1

HCID 10026851HCID 10026851、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 1,2,3,4-tetrahydro-2-naphthoic acid (Aldrich, 0.50 g, 2.8 mmol) in methylene chloride (10 mL) at 0° C. was added a drop of dimethylformamide and oxalyl chloride (2 M in methylene chloride, 4.3 mL, 8.5 mmol). After stirring at room temperature for 2 h, the reaction mixture was concentrated on a rotary evaporator and dried under vacuum, and the resulting crude acyl chloride (0.55 g) was used without further purification. Thus, the crude acyl chloride (88 mg, 0.45 mmol) was dissolved in 1 mL of methylene chloride and was added 3,4-bis(4-chlorophenyl)-1-methylpropyl-amine hydrochloride salt (Reference Example 1) (Diastereomer α, 0.10 g, 0.30 mmol) and diisopropylethylamine (0.16 mL, 0.91 mmol). After stirring at room temperature for 6 h, the reaction mixture was loaded onto a silica gel column, which was eluted with 10% ethyl acetate to give a faster eluting diastereomer (Diastereomer I) and a slower eluting diastereomer (Diastereomer II) along with some mixed fractions.

後処理

  1. concentrationthe reaction mixture was concentrated on a rotary evaporator
  2. customdried under vacuum
  3. customthe resulting crude acyl chloride (0.55 g) was used without further purification
  4. stirringAfter stirring at room temperature for 6 h
  5. washwas eluted with 10% ethyl acetate
  6. customto give
  7. washa faster eluting diastereomer (Diastereomer I)
  8. washa slower eluting diastereomer (Diastereomer II) along with some mixed fractions

出典と根拠

ORDレコード
ord-1f87624d07244d6790e6481f8bf7a092
出典データセット
uspto-grants-2010_02
特許番号
US07667053B2

反応ノート

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