1,2-Dichloroethane → Tert-butyl 1-amino-4,4,4-trifluoro-1-oxobutan-2-ylcarbamate

HRID 84923Notes

Reaction equation

HRID 84923 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]([F:17])([F:16])[F:15])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=C2[N:24]=NN(O)C2=CC=1.O.C(Cl)CCl.[NH4+].[OH-]>CN(C=O)C.CCOC(C)=O.O>[NH2:24][C:10](=[O:11])[CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][C:14]([F:17])([F:16])[F:15]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 27960291-Hydroxybenzotriazole hydrateHCID 120980572-(((Tert-butoxy)carbonyl)amino)-4,4,4-trifluorobutanoic acid

Product 1

HCID 86666168Tert-butyl 1-amino-4,4,4-trifluoro-1-oxobutan-2-ylcarbamate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(tert-butoxycarbonylamino)-4,4,4-trifluorobutanoic acid (370 mg, 1.43 mmol) and HOBt hydrate (264 mg, 1.72 mmol) in DMF (5 mL), EDC (332 mg, 1.72 mmol) was added. After being stirred at room temperature for 1 h, conc. NH4OH (14 N, 0.600 mL, 8.40 mmol) was added. The mixture was stirred for 18 h. Water and EtOAc were added. The organic phase was washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give tert-butyl 1-amino-4,4,4-trifluoro-1-oxobutan-2-ylcarbamate as a solid.

Workup

  1. stirringThe mixture was stirred for 18 h
  2. washThe organic phase was washed with 5% NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-adbd88f9e6ce40a1b2ec65437cae4257
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

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