Trifluoroacetic acid → HCID 68687078, compound

HRID 638962Notes

Reaction equation

HRID 638962 reaction equation
C([O:5][C:6]([C@H:8]1[C@H:11]([CH2:12][CH3:13])[CH2:10][N:9]1[C:14](=[O:28])[C:15]1[CH:20]=[C:19]([CH2:21][CH2:22][CH3:23])[C:18]([O:24][CH3:25])=[C:17]([O:26][CH3:27])[CH:16]=1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:27][O:26][C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([CH2:21][CH2:22][CH3:23])[C:18]=1[O:24][CH3:25])[C:14]([N:9]1[CH2:10][C@@H:11]([CH2:12][CH3:13])[C@@H:8]1[C:6]([OH:7])=[O:5])=[O:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68685720HCID 68685720, compound

Product 1

HCID 68687078HCID 68687078, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (+)-trans-1-(3,4-dimethoxy-5-propylbenzoyl)-3-ethylazetidine-2-carboxylic acid tert-butyl ester (160 mg, 0.41 mmol, 1 eq.) in dry DCM (3.5 mL) at room temperature was added TFA (1.5 mL). The resulting reaction mixture stirred at room temperature for 2 h. The solvent was removed in vacuo and dried under high vacuum. The residue was dissolved in ether and washed with 2% NaOH solution. The aqueous layer was acidified with 1 M HCl and extracted with EtOAc. The organic layer dried over Na2SO4, filtered, and concentrated in vacuo to afford (+)-trans-1-(3,4-dimethoxy-5-propylbenzoyl)-3-ethylazetidine-2-carboxylic acid in 80% yield, which was used without further purification. ESMS: m/z 336.3 [M+H].

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent was removed in vacuo
  3. customdried under high vacuum
  4. dissolutionThe residue was dissolved in ether
  5. washwashed with 2% NaOH solution
  6. extractionextracted with EtOAc
  7. dry with materialThe organic layer dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-675579b7b06d41aa8cc2492170e3d0aa
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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