Reaction #41272

Reaction equation

Ethylbromide

compound 10

{3-[(Anthracen-9-ylmethyl)-amino]-propyl}-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester

K2CO3

→

11

Yield 80.0%

[3-(Anthracen-9-ylmethyl-ethyl-amino)-propyl]-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester

Yield 80.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   ConcentrationAfter the confirmation of the disappearance of the 10 by TLC, the solution was concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2 (20 mL)
3. 3
   Washwashed three times with aqueous sodium carbonate
4. 4
   OtherThe organic layer was separated
5. 5
   Dryingdried with anhydrous Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated under vacuum

Procedure

Ethylbromide (EtBr, 508 mg, 4.66 mmol) was dissolved in anhydrous acetonitrile and added to a stirring mixture of compound 10 (805 mg, 1.55 mmol) and anhydrous K2CO3 (644 mg, 4.66 mmol). The mixture was then stirred overnight at 75° C. under a N2 atmosphere. After the confirmation of the disappearance of the 10 by TLC, the solution was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (20 mL) and washed three times with aqueous sodium carbonate. The organic layer was separated, dried with anhydrous Na2SO4, filtered and concentrated under vacuum. Flash column chromatography of the residue gave 11 as a light yellow oil. Yield 80%; Rf=0.35 (3% MeOH/CHCl3); 1H NMR (CDCl3) δ 8.43 (d, 2H), 8.25 (s, 1H), 7.86 (d, 2H), 7.43 (m, 2H), 7.37 (m, 2H), 4.34 (s, 2H), 2.78-2.92 (m, 4H), 2.64 (m, 4H), 2.36 (m, 2H), 1.21-1.48 (m, 23H), 1.16 (m, 2H); 13C NMR (CDCl3) δ 155.7, 131.1 (3C), 131.0, 128.7 (2C), 127.0 (2C), 125.2 (2C), 124.8 (2C), 124.5 (2C), 78.9, 78.4, 53.4, 50.6, 50.0, 47.9, 45.3, 43.5, 37.1, 28.3 (6C), 26.5, 11.7. HRMS (FAB) m/z calcd. for C33H47N3O4 (M+H)+ 550.3639, found 550.3619.

Source