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

HRID 219878노트

반응식

HRID 219878 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

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.), 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%).

후처리

  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

출처 및 근거

ORD 기록
ord-aa8828141f2547d6805209557794760e
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202865B2

반응 노트

불러오는 중…