Dichloromethane → (R)-2-amino-3-methyl-N-(2,2,2-trifluoroethyl)butanamide hydrochloride

HRID 510178Notes

Reaction equation

HRID 510178 reaction equation
[CH3:1][CH:2]([CH3:20])[C@@H:3]([NH:12]C(=O)OC(C)(C)C)[C:4](=[O:11])[NH:5][CH2:6][C:7]([F:10])([F:9])[F:8].C(O)(C(F)(F)F)=O.C(Cl)[Cl:29]>>[ClH:29].[NH2:12][C@H:3]([CH:2]([CH3:20])[CH3:1])[C:4]([NH:5][CH2:6][C:7]([F:8])([F:9])[F:10])=[O:11]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 117628462(R)-tert-butyl 3-methyl-1-oxo-1-(2,2,2-trifluoroethylamino)butan-2-ylcarbamate

Product 1

HCID 117628603(R)-2-amino-3-methyl-N-(2,2,2-trifluoroethyl)butanamide hydrochloride

Procedure

(R)-tert-butyl 3-methyl-1-oxo-1-(2,2,2-trifluoroethylamino)butan-2-ylcarbamate I-3a (12.81 g, 42.9 mmol) was dissolved in DCM (30 ml), and TFA (12 ml, 156 mmol) slowly added. The reaction was allowed to stir at room temperature for 2 hr. The mixture was concentrated in vacuo to an oil. The oil was dissolved in DCM and washed with aq. sodium bicarbonate (50 mL) dried over sodium sulfate, filtered and concentrated to an oil. The oil was dissolved in ethyl acetate, cooled to 0° C. and treated with 1N HCL in diethyl ethere to give upon filtration 10.0 gm solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo to an oil
  2. dissolutionThe oil was dissolved in DCM
  3. washwashed with aq. sodium bicarbonate (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. dissolutionThe oil was dissolved in ethyl acetate
  8. temperaturecooled to 0° C.
  9. additiontreated with 1N HCL in diethyl

Sources & evidence

ORD record
ord-ba2873096b3b4172ba1fd7e2af234aeb
Source dataset
uspto-grants-2015_08
Patent number
US09096598B2

Reaction notes

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