Potassium Carbonate → tert-butyl N-(5-cyano-2-fluorobenzyl)-N-methylglycinate

HRID 219878ノート

反応式

HRID 219878 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].Cl.[C:13]([O:17][C:18](=[O:22])[CH2:19][NH:20][CH3:21])([CH3:16])([CH3:15])[CH3:14].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:20]([CH3:21])[CH2:19][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:22])#[N:2]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 11252350Sarcosine t-butyl ester hydrochlorideHCID 162272363-(Bromomethyl)-4-fluorobenzonitrile

生成物 1

HCID 67529926tert-butyl N-(5-cyano-2-fluorobenzyl)-N-methylglycinate

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.), sarcosine tert-butyl ester hydrochloride (BACHEM; F-1135; 1 527.73 mg; 8.41 mmol; 1.20 eq.) and potassium carbonate (2.91 g; 21.02 mmol; 3 eq.) in CH3CN (25 mL) was stirred at 60° C. for 6 hours then at RT for one night. The acetonitrile was evaporated in vacuo and the resulting mixture diluted with water. Extraction with EtOAc, washing with NaCl sat. solution, drying over magnesium sulfate and concentration in vacuo gave the title compound as a slightly yellow oil (1.9 g; 97%). 1H NMR (CDCl3) δ 7.86 (dd, J=6.5, 2.0 Hz, 1H), 7.59-7.53 (m, 1H), 7.13 (t, J=9.0 Hz, 1H), 3.78 (s, 2H), 3.23 (s, 2H), 2.38 (s, 3H), 1.49 (s, 9H). 19F NMR (CDCl3) δ-108.3. GC/MS: 278. LC/MS (Method B): 279.1 (M+H)+. HPLC (Method A) Rt 2.25 min (Purity: 91.4%).

後処理

  1. waitat RT for one night
  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 magnesium sulfate and concentration in vacuo

出典と根拠

ORDレコード
ord-aa8828141f2547d6805209557794760e
出典データセット
uspto-grants-2012_06
特許番号
US08202865B2

反応ノート

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