4-Toluenesulfonyl chloride → (3S,5R)-5-Methyl-3-(toluene-4-sulfonyloxymethyl)nonanoic acid tert-butyl ester

HRID 479055ノート

反応式

HRID 479055 の反応式
[C:1]([O:5][C:6](=[O:18])[CH2:7][C@@H:8]([CH2:16][OH:17])[CH2:9][C@H:10]([CH3:15])[CH2:11][CH2:12][CH2:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:18])[CH2:7][C@@H:8]([CH2:16][O:17][S:25]([C:22]1[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=1)(=[O:27])=[O:26])[CH2:9][C@H:10]([CH3:15])[CH2:11][CH2:12][CH2:13][CH3:14])([CH3:3])([CH3:2])[CH3:4]

参加物

6

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 57065055(3S,5R)-3-Hydroxymethyl-5-methyl-nonanoic Acid Tert-butyl Ester

生成物 1

HCID 57230188(3S,5R)-5-Methyl-3-(toluene-4-sulfonyloxymethyl)nonanoic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To alcohol 140 (6.14 mmol) in 30 mL CH2Cl2 at 0° C. was added DMAP (0.1 g), p-toluenesulfonyl chloride (1.37 g, 7.2 mmol), and then triethylamine (1.8 mL, 13 mmol) was added quickly dropwise. The mixture was warmed immediately to ambient temperature following addition and stirred overnight, and did not proceed to completion. The mixture was partitioned between Et2O and 1N HCl (aq), the phases were separated, and the organic phase washed with sat. NaHCO3 (aq), dried (MgSO4), and concentrated to provide tosylate 141. The product was used without further purification.

後処理

  1. additionaddition
  2. customThe mixture was partitioned between Et2O and 1N HCl (aq)
  3. customthe phases were separated
  4. washthe organic phase washed with sat. NaHCO3 (aq)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-5fc3e3025df24178a00ac60ffc518251
出典データセット
uspto-grants-2003_11
特許番号
US06642398B2

反応ノート

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