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

HRID 70861

반응식

HRID 70861 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-8c810a774a2649eab9bd1d9a1924ef82
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822534B2

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