Trifluoroacetic acid → HCID 178502740, compound

HRID 271349Notes

Reaction equation

HRID 271349 reaction equation
C([O:5][C:6](=[O:18])[CH2:7][C@H:8]1[CH2:11][C@@H:10]([C:12](=[O:17])[N:13]([O:15][CH3:16])[CH3:14])[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:16][O:15][N:13]([CH3:14])[C:12]([C@@H:10]1[CH2:11][C@H:8]([CH2:7][C:6]([OH:18])=[O:5])[CH2:9]1)=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178502741HCID 178502741, compound

Product 1

HCID 178502740HCID 178502740, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of 2 g of cis-[3-(methoxy-methyl-carbamoyl)-cyclobutyl]-acetic acid tert-butyl ester in 25 mL of dichloromethane was added 10 mL of trifluoroacetic acid. The mixture was allowed to warm and stir for 2 h then concentrated under reduced pressure. The residue was taken up in 3×50 mL of toluene and repeatedly concentrated under reduced pressure to remove trifluoroacetic acid. Drying under vacuum overnight gave 1.6 g of product as a colorless oil: MS (m+1)=202.3; 1H NMR (400 MHz, CDCl3) 9.0 (br s, 1H), 3.62 (s, 3H), 3.18 (s, 3H), 2.65 (m, 1H), 2.5 (overlapping d and m, 3H), 2.4 (dd, 1H), 2.0 (, m, 2H).

Workup

  1. temperatureto warm
  2. concentrationthen concentrated under reduced pressure
  3. concentrationrepeatedly concentrated under reduced pressure
  4. customto remove trifluoroacetic acid
  5. customDrying under vacuum overnight

Sources & evidence

ORD record
ord-860d91fe54e443459ff03a0de0adcc89
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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