Potassium Carbonate → tert-butyl N-(5-cyano-2-fluorobenzyl)-N-methyl-beta-alaninate

HRID 219885노트

반응식

HRID 219885 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([F:11])=[C:7]([CH:10]=1)[CH2:8]Br)#[N:2].[CH3:12][NH:13][CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CC#N>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([F:11])=[C:7]([CH:10]=1)[CH2:8][N:13]([CH3:12])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])#[N:2]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 14760311Tert-butyl 3-(methylamino)propanoateHCID 162272363-(Bromomethyl)-4-fluorobenzonitrile

생성물 1

HCID 66677998tert-butyl N-(5-cyano-2-fluorobenzyl)-N-methyl-beta-alaninate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

A mixture of 5-cyano-2-fluorobenzylbromide (CARBOCORE; CO-0137; 1.50 g; 7.01 mmol; 1 eq.), tert-butyl N-methyl-beta-alaninate (1.34 g; 8.41 mmol; 1.20 eq.) (prepared as described by Howard N., I. et al. in Bioorg. Med. Chem. 11 (2003), 3083-3099) and potassium carbonate (1.94 g; 14.02 mmol; 2 eq.) in CH3CN (25 mL) was stirred at 60° C. for 6 hours then at RT for 16 hours. The acetonitrile was evaporated in vacuo and the resulting mixture diluted with water. Extraction with EtOAc, washing with NaCl sat. solution, drying over sodium sulfate and concentration in vacuo gave title compound as a slightly yellow oil (1.9 g; 92%). 1H NMR (CDCl3) δ 7.79 (dd, J=6.7, 2.1 Hz, 1H), 7.57-7.52 (m, 1H), 7.11 (t, J=8.9 Hz, 1H), 3.57 (s, 2H), 2.74 (t, J=7.1 Hz, 2H), 2.43 (t, J=7.1 Hz, 2H), 2.22 (s, 3H), 1.45 (s, 9H). LC/MS (Method B): 293.2 (M+H)+. HPLC (Method A) Rt 2.44 min (Purity: 86.4%).

후처리

  1. waitat RT for 16 hours
  2. customThe acetonitrile was evaporated in vacuo
  3. additionthe resulting mixture diluted with water
  4. extractionExtraction with EtOAc
  5. washwashing with NaCl sat. solution
  6. dry with materialdrying over sodium sulfate and concentration in vacuo

출처 및 근거

ORD 기록
ord-c8ca3a328c884567a1cdf62584df45a8
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202865B2

반응 노트

불러오는 중…