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

HRID 219878Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219878
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-aa8828141f2547d6805209557794760e
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202865B2

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