1,2-Dichloroethane → Benzyl 1-amino-4,4,4-trifluoro-1-oxobutan-2-ylcarbamate

HRID 2201118Notes

Reaction equation

HRID 2201118 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:16][C:17]([F:20])([F:19])[F:18])[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C2[N:27]=NN(O)C2=CC=1.O.C(Cl)CCl.[NH4+].[OH-]>CN(C=O)C.CCOC(C)=O.O>[NH2:27][C:13](=[O:14])[CH:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:16][C:17]([F:20])([F:19])[F:18]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 27960291-Hydroxybenzotriazole hydrateHCID 184660582-{[(Benzyloxy)carbonyl]amino}-4,4,4-trifluorobutanoic acid

Product 1

HCID 67515558Benzyl 1-amino-4,4,4-trifluoro-1-oxobutan-2-ylcarbamateYield 87.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(benzyloxycarbonylamino)-4,4,4-trifluorobutanoic acid (200 mg, 0.687 mmol), HOBt monohydrate (137 mg, 0.895 mmol) and EDC (171 mg, 0.890 mmol) in DMF (5 mL) was stirred at room temperature for 15 min, conc. NH4OH (0.250 mL, ca. 3.50 mmol) was added. The mixture was stirred at room temperature for 18 h. Water and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give benzyl 1-amino-4,4,4-trifluoro-1-oxobutan-2-ylcarbamate (175 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with 5% NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1274a3f3cd64fb2b589203ad66a75bd
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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