Trifluoroacetic acid → HCID 66653346, compound

HRID 1524278Notes

Reaction equation

HRID 1524278 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C@H:11]([C:13]([O:15]C(C)(C)C)=[O:14])[CH3:12])[CH:5]=1.FC(F)(F)C(O)=O>C(Cl)Cl.O>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C@H:11]([C:13]([OH:15])=[O:14])[CH3:12])[CH:5]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66653468HCID 66653468, compound

Product 1

HCID 66653346HCID 66653346, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Cool a solution of 3-((S)-1-tert-butoxycarbonyl-ethoxy)-benzoic acid methyl ester (0.80 g, 2.85 mmol) in methylene chloride (10 mL) to 0° C. and add trifluoroacetic acid (0.98 g 8.60 mmol). Warm the mixture to room temperature and stir overnight. Dilute the mixture with water and extract with methylene chloride. Concentrate the combined organic phase under reduced pressure and purify the residue by trituration with hexanes and methylene chloride to provide 0.40 g of 3-((S)-1-carboxy-ethoxy)-benzoic acid methyl ester as a solid.

Workup

  1. extractionextract with methylene chloride
  2. concentrationConcentrate the combined organic phase under reduced pressure
  3. custompurify the residue by trituration with hexanes and methylene chloride

Sources & evidence

ORD record
ord-b8f8651b3954433b9471c0fc1f62093c
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

Loading…