Trifluoroacetic acid → HCID 68459863, compound

HRID 751170Notes

Reaction equation

HRID 751170 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@@H:9]1[C@H:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26]([Cl:32])[C:25]=1[CH3:33])[CH3:22])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.CCOC(C)=O>[Si:14]([O:13][C@H:10]1[CH2:11][CH2:12][NH:8][C@@H:9]1[C@H:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26]([Cl:32])[C:25]=1[CH3:33])[CH3:22])([C:17]([CH3:19])([CH3:20])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68459554(2S,3S)-1-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-[(1R)-1-(3-chloro-4-cyano-2-methylphenylamino)ethyl]pyrrolidine

Product 1

HCID 68459863HCID 68459863, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Intermediate 80E (36 mg, 0.073 mmol) was dissolved in DCM (900 μL) and TFA (100 μL) was added. The mixture was stirred at rt for 10 h. The reaction was diluted with EtOAc, washed with saturated sodium bicarbonate solution (3×5 mL), brine (5 mL), dried (MgSO4), filtered and concentrated to give the title compound 80F (27 mg): MS (ES) m/z 394.5 [M+H]+.

Workup

  1. washwashed with saturated sodium bicarbonate solution (3×5 mL), brine (5 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5c5bffc4f7f1412db92061ca1ab657be
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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