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Aniline → ethyl (2S)-2-anilinopropanoate

HRID 530108
ノート
印刷プレビュー

反応式

HRID 530108 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.FC(F)(F)S(O[CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])(=O)=O>ClCCl>[C:2]1([NH:1][C@H:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:27])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6115AnilineHCID 8471TriethylamineHCID 4251232Ethyl (-)-lactate triflate

生成物 1

HCID 21124386ethyl (2S)-2-anilinopropanoate収率 92.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
35 °C

実験手順

To a stirred solution of aniline (4.55 mL, 50 mmol) and triethylamine (7 mL, 50 mmol) in anhydrous dichloromethane (120 mL) was added a solution of ethyl 2-{[(trifluoromethyl)sulfonyl]oxy}propanoate (12.5 g, 50 mmol) in dichloromethane (60 mL) at 0° C. (Ice bath) over a period of 30 minutes under nitrogen. The ice bath was then removed and the reaction mixture was stirred at 35° C. for 2 h. The reaction mixture was cooled to rt, washed with water, dried over sodium sulfate, and evaporated to give desired product as oil (8.9 g, 92%) which was used as such for the next step. 1HNMR (300 MHz, CDCl3): δ 1.19-1.67 (m, 6H), 4.17-4.38 (m, 3H), 6.65-6.80 (m, 3H), 7.20-7.35 (m, 2H).

後処理

  1. customThe ice bath was then removed
  2. temperatureThe reaction mixture was cooled to rt
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated

出典と根拠

ORDレコード
ord-bb4eed0f32d84b60b3e2ecdb0dcbb0dc
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09351974B2

反応ノート

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