Trifluoromethanesulfonic anhydride → HCID 86598333, compound

HRID 1393389Notes

Reaction equation

HRID 1393389 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[CH2:16]([O:18][C:19](=[O:36])[C@H:20]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31](O)[CH:30]=1)[NH:21][C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[CH3:17]>N1C=CC=CC=1>[CH2:16]([O:18][C:19](=[O:36])[C@H:20]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])[CH:30]=1)[NH:21][C:22](=[O:27])[C:23]([F:24])([F:25])[F:26])[CH3:17]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 86598324HCID 86598324, compound

Product 1

HCID 86598333HCID 86598333, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Trifluoromethanesulfonic anhydride (1.51 ml) was added dropwise to an ice-cold solution of N-trifluoroacetyl-3-hydroxy-L-phenylalanine ethyl ester (915 mg, 3.00 mmol) in pyridine (9 ml) in 5 minutes under argon atmosphere. The mixture was stirred at the same temperature for 30 minutes and then at room temperature for 16 hrs. The reaction mixture was poured into ice-water (500 ml) and extracted with ethyl acetate. The extract was washed with 10% hydrochloric acid, water and brine in turn and then dried. The solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=7) to give N-trifluoroacetyl-3-trifluoromethanesulfonyloxy-L-phenylalanine ethyl ester (1.25 g, 95%) as pale yellow crystals.

Workup

  1. waitat room temperature for 16 hrs
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 10% hydrochloric acid, water and brine in turn
  4. customdried
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=7)

Sources & evidence

ORD record
ord-8672a4d433cb4878b80f20a700bb12f8
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

Loading…