Benzyl chloroformate → 2-{[(Benzyloxy)carbonyl]amino}-4,4,4-trifluorobutanoic acid

HRID 2201117Notes

Reaction equation

HRID 2201117 reaction equation
[NH2:1][CH:2]([CH2:6][C:7]([F:10])([F:9])[F:8])[C:3]([OH:5])=[O:4].[OH-].[Na+].Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>O1CCOCC1>[CH2:17]([O:16][C:14]([NH:1][CH:2]([CH2:6][C:7]([F:10])([F:9])[F:8])[C:3]([OH:5])=[O:4])=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 3530832-Amino-4,4,4-trifluorobutanoic acid

Product 1

HCID 184660582-{[(Benzyloxy)carbonyl]amino}-4,4,4-trifluorobutanoic acidYield 20.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-4,4,4-trifluorobutyric acid (543 mg, 3.45 mmol) in aq. 1N NaOH (13 mL, 13.0 mmol), a solution of benzyl chloroformate (0.600 mL, 4.26 mmol) in dioxane (5 mL) was added. The mixture was stirred at room temperature for 18 h. It was then washed with EtOAc. The aqueous solution was acidified to pH 1-2 with 6N HCl. The product was extracted with EtOAc. The EtOAc phase was dried over Na2SO4, concentrated in vacuo to give 2-(benzyloxycarbonylamino)-4,4,4-trifluorobutanoic acid (202 mg).

Workup

  1. washIt was then washed with EtOAc
  2. extractionThe product was extracted with EtOAc
  3. dry with materialThe EtOAc phase was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bba1a193d47741a5863073669067a77d
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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