Iodoethane → (R)-Ethyl 4-(4-bromophenyl)-3-((tert-butoxycarbonyl)amino)butanoate

HRID 70861

反応式

HRID 70861 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[CH2:27](I)[CH3:28]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C@@H:9]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][C:11]([O:13][CH2:27][CH3:28])=[O:12])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6340IodoethaneHCID 516892Sodium BicarbonateHCID 7009737(3R)-4-(4-bromophenyl)-3-{[(tert-butoxy)carbonyl]amino}butanoic acid

生成物 1

HCID 59607624(R)-Ethyl 4-(4-bromophenyl)-3-((tert-butoxycarbonyl)amino)butanoate収率 95.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of (R)-4-(4-bromophenyl)-3-(tert-butoxycarbonylamino)butanoic acid (9.98 g, 27.9 mmol) and NaHCO3 (4.68 g, 55.7 mmol) in DMF (45 mL) is added Ethyl iodide (6.75 mL, 84 mmol) at room temperature under nitrogen. After stirring for 71 hours, the reaction is quenched with H2O (300 mL), and then precipitated solid is collected and washed with H2O (500 mL) to give (R)-ethyl 4-(4-bromophenyl)-3-(tert-butoxycarbonylamino)butanoate (10.25 g, 94%). HPLC retention time=1.48 minutes (condition B); MS (ES+)=329.9 (m-tBu+2); 286.0 (m-Boc+2; 100%); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.27 (t, J=7.2 Hz, 3 H) 1.40 (s, 9 H), 2.43 (A of ABX, Jab=15.8 Hz, Jax=5.7 Hz, 1 H) 2.50 (B of ABX, Jab=15.8 Hz, Jbx=5.4 Hz, 1 H) 2.74-2.90 (m, 2 H) 4.11 (br s) 4.15 (q, J=7.1 Hz, 2 H) 5.04 (br d) 7.07 (d, J=8.3 Hz, 2 H) 7.40-7.43 (m, 2 H).

後処理

  1. customthe reaction is quenched with H2O (300 mL)
  2. customprecipitated solid
  3. customis collected
  4. washwashed with H2O (500 mL)

出典と根拠

ORDレコード
ord-8c810a774a2649eab9bd1d9a1924ef82
出典データセット
uspto-grants-2014_09
特許番号
US08822534B2

関連ノート

読み込み中…