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

HRID 219885ノート

反応式

HRID 219885 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-c8ca3a328c884567a1cdf62584df45a8
出典データセット
uspto-grants-2012_06
特許番号
US08202865B2

反応ノート

読み込み中…