Trifluoroacetic acid → HCID 68028646, compound

HRID 452860Notes

Reaction equation

HRID 452860 reaction equation
[OH:1][C@H:2]1[C@H:6]([NH:7][C:8]([O:10][C@@H:11]([CH3:16])[C:12]([F:15])([F:14])[F:13])=[O:9])[CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[OH:1][C@@H:2]1[CH2:3][NH:4][CH2:5][C@H:6]1[NH:7][C:8](=[O:9])[O:10][C@@H:11]([CH3:16])[C:12]([F:13])([F:14])[F:15]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 66709356HCID 66709356, compound

Product 1

HCID 68028646HCID 68028646, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To the solution of tert-butyl (3R,4R)-3-hydroxy-4-[({[(2S)-1,1,1-trifluoropropan-2-yl]oxy}carbonyl)amino]pyrrolidine-1-carboxylate (100 mg) in CHCl3 (0.5 ml) was added TFA (0.5 ml). After stirring for 1 hour at room temperature, the mixture was poured into saturated aqueous solution of NaHCO3 and extracted with CHCl3. The extract was dried over Na2SO4 and concentrated to give (2S)-1,1,1-trifluoropropan-2-yl [(3R,4R)-4-hydroxypyrrolidin-3-yl]carbamate as a pale yellow foam.

Workup

  1. extractionextracted with CHCl3
  2. dry with materialThe extract was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6c8fa94c89c949da8aefd4dc234f8641
Source dataset
uspto-grants-2013_07
Patent number
US08492397B2

Reaction notes

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