4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 2-(4-chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-3-hydroxy-2-hydroxymethyl-propyl ester

HRID 82249ノート

反応式

HRID 82249 の反応式
C(N(CC)CC)C.Cl.CN(C)C.[Cl:13][C:14]1[C:15]2[CH:22]=[CH:21][N:20]([C:23]([CH2:28][OH:29])([CH2:26][OH:27])[CH2:24][OH:25])[C:16]=2[N:17]=[CH:18][N:19]=1.[S:30](Cl)([C:33]1[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=1)(=[O:32])=[O:31]>ClCCl.O>[Cl:13][C:14]1[C:15]2[CH:22]=[CH:21][N:20]([C:23]([CH2:24][OH:25])([CH2:28][OH:29])[CH2:26][O:27][S:30]([C:33]3[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[C:16]=2[N:17]=[CH:18][N:19]=1

参加物

7

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10313079Trimethylamine HydrochlorideHCID 866721162-(4-Chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-2-hydroxymethyl-propane-1,3-diol

生成物 1

HCID 86672115Toluene-4-sulfonic acid 2-(4-chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-3-hydroxy-2-hydroxymethyl-propyl ester収率 55%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

Triethylamine (0.879 mL, 6.31 mmol) and trimethylamine hydrochloride (253 mg, 2.65 mmol) were added to a solution of 2-(4-chloro-pyrrolo[2,3-d]pyrimidin-7-yl)-2-hydroxymethyl-propane-1,3-diol (Preparation 209, 650 mg, 2.52 mmol) in dichloromethane (20 mL) at 00° C. The mixture was treated portion-wise with tosyl chloride (505 mg, 2.65 mmol) and stirred at 00° C. for 16 hours. The reaction mixture was treated with water and stirred for 10 min. The resulting mixture was washed with citric acid, saturated aqueous sodium bicarbonate, and saturated brine, then evaporated in vacuo. The crude product was purified by column chromatography on silica gel (gradient of EtOAc:DCM 0:100 to 30:70) to afford the title compound as a colorless solid in 55% yield, 570 mg.

後処理

  1. stirringstirred for 10 min
  2. washThe resulting mixture was washed with citric acid, saturated aqueous sodium bicarbonate, and saturated brine
  3. customevaporated in vacuo
  4. customThe crude product was purified by column chromatography on silica gel (gradient of EtOAc:DCM 0:100 to 30:70)

出典と根拠

ORDレコード
ord-1df82f74d2d248578016e252c28a42bd
出典データセット
uspto-grants-2014_09
特許番号
US08846698B2

反応ノート

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