Trifluoroacetic acid → HCID 53648487, compound

HRID 254797Notes

Reaction equation

HRID 254797 reaction equation
C([O:5][C:6](=[O:22])[CH2:7][C@@H:8]([CH2:19][CH2:20][CH3:21])[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:12]([O:11][C:9](=[O:10])[C@H:8]([CH2:19][CH2:20][CH3:21])[CH2:7][C:6]([OH:22])=[O:5])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18644119HCID 18644119, compound

Product 1

HCID 53648487HCID 53648487, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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).

Workup

  1. concentrationbefore being concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dry DCM
  3. concentrationbefore concentrating again
  4. customto remove excess trifluoroacetic acid

Sources & evidence

ORD record
ord-932680139ab64ae8bd05b93aaf5d12b6
Source dataset
uspto-grants-2011_01
Patent number
US07875712B2

Reaction notes

Loading…