4-Toluenesulfonyl chloride → 1-(4-Methoxy-benzoyl)-3-(toluene-4-sulfonyloxymethyl)-pyrrolidine-3-carboxylic acid ethyl ester

HRID 2060240ノート

反応式

HRID 2060240 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.Cl.CN(C)C.[CH2:17]([O:19][C:20]([C:22]1([CH2:37][OH:38])[CH2:26][CH2:25][N:24]([C:27](=[O:36])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH2:23]1)=[O:21])[CH3:18].C(N(CC)CC)C>ClCCl.O>[CH2:17]([O:19][C:20]([C:22]1([CH2:37][O:38][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:26][CH2:25][N:24]([C:27](=[O:36])[C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)[CH2:23]1)=[O:21])[CH3:18]

参加物

7

反応物 4

HCID 73974-Toluenesulfonyl chloride2 回HCID 8471TriethylamineHCID 10313079Trimethylamine Hydrochloride2 回HCID 593222033-Hydroxymethyl-1-(4-methoxy-benzoyl)-pyrrolidine-3-carboxylic acid ethyl ester

生成物 1

HCID 593222061-(4-Methoxy-benzoyl)-3-(toluene-4-sulfonyloxymethyl)-pyrrolidine-3-carboxylic acid ethyl ester収率 101.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

4-Toluenesulphonyl chloride (131 g, 687 mmol) and trimethylamine hydrochloride (43.8 g, 458 mmol) were added to 3-hydroxymethyl-1-(4-methoxy-benzoyl)-pyrrolidine-3-carboxylic acid ethyl ester (140.7 g, 457.8 mmol) (see Preparation 10) and triethylamine (160 mL, 1140 mmol) in dichloromethane (1400 mL) at 0° C. The reaction mixture was stirred at 0° C. for 4 hours then at RT for 18 hours. Cooled to 0° C. and trimethylamine hydrochloride (21.9 g, 229 mmol) was added, followed by 4-toluenesulphonyl chloride (17.45 g, 91.6 mmol). The reaction mixture was stirred at 0° C. for 4 hours. Water (500 mL) was added and stirred for 10 minutes. The reaction mixture was washed with 2M citric acid aqueous solution (1400 mL) and saturated aqueous NaHCO3 (1400 mL). The organic layer was separated, washed with water (1300 mL) then concentrated under reduced pressure to afford the title compound as a brown oil (215.15 g, 100%).

後処理

  1. waitat RT for 18 hours
  2. temperatureCooled to 0° C.
  3. stirringThe reaction mixture was stirred at 0° C. for 4 hours
  4. stirringstirred for 10 minutes
  5. washThe reaction mixture was washed with 2M citric acid aqueous solution (1400 mL) and saturated aqueous NaHCO3 (1400 mL)
  6. customThe organic layer was separated
  7. washwashed with water (1300 mL)
  8. concentrationthen concentrated under reduced pressure

出典と根拠

ORDレコード
ord-eec50096fc6b433581a50f7a05d644a7
出典データセット
uspto-grants-2012_10
特許番号
US08278343B2

反応ノート

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