Trifluoroacetic acid → HCID 50999035, compound

HRID 2279254Notes

Reaction equation

HRID 2279254 reaction equation
[CH3:1][N:2]1[CH2:6][C@H:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[N:4](C(OC(C)(C)C)=O)[C:3]1=[O:24].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][N:2]1[CH2:6][C@H:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[NH:4][C:3]1=[O:24]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 66981144HCID 66981144, compound

Product 1

HCID 50999035HCID 50999035, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-1-tert-butyl 5-benzyl 3-methyl-2-oxoimidazolidine-1,5-dicarboxylate (25b) (0.650 g, 1.95 mmol) in DCM (20 mL), cooled to 0° C., TFA (3 mL, 2.9 mmol) was added. The reaction mixture was slowly warmed to room temperature and stirred for further 1 h. After completion (by TLC), the reaction mixture was neutralized with saturated NaHCO3 solution and extracted with EtOAc (3×10 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to provide the crude residue which was purified by column chromatography to furnish 25c (0.320 g, 70%) as off white solid.

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto provide the crude residue which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-5c9563c3ce1046f7ad3c709b1af1e111
Source dataset
uspto-grants-2015_09
Patent number
US09133182B2

Reaction notes

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