Reaction #985319

Reaction equation

(2R)-2-propyl-succinic acid 1-benzyl ester 4-tert-butyl ester

trifluoroacetic acid

→

sub-title compound

Yield 99.3%

(2R)-2-Propyl-succinic acid 1-benzyl ester

Yield 99.3%

Solvents

DCM

DCM

Conditions

Workup

1. 1
   Concentrationbefore being concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in dry DCM
3. 3
   Concentrationbefore concentrating again
4. 4
   Otherto remove excess trifluoroacetic acid

Procedure

A stirred solution of (2R)-2-propyl-succinic acid 1-benzyl ester 4-tert-butyl ester (4.56 g, 14.88 mmol) in anhydrous DCM (20 mL), at 0° C., was treated with a solution of trifluoroacetic acid (10 mL) in anhydrous DCM (10 mL). The reaction mixture was allowed to warm to ambient temperature over 3 h before being concentrated under reduced pressure. The residue was dissolved in dry DCM, before concentrating again. This process was repeated several times in order to remove excess trifluoroacetic acid to leave the sub-title compound (3.70 g, 99%) as a gum: 1H NMR (400 MHz, CDCl3) δ 0.82-0.99 (3H, m), 1.21-1.76 (4H, m), 2.45-2.60 (1H, m), 2.76-3.00 (2H, m), 5.10-5.21 (2H, m), 7.28-7.43 (5H, m), 7.83-8.18 (1H, m).

Source