Trifluoroacetic acid → HCID 23648567, compound

HRID 2096921Notes

Reaction equation

HRID 2096921 reaction equation
[CH2:1]([NH:8][C:9](=[O:24])[C@H:10]([NH:16][C:17](=O)[O:18]C(C)(C)C)[CH2:11][O:12][CH:13]([F:15])[F:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:26](F)(F)C(O)=O>ClCCl>[C:17]([NH:16][C@H:10]([CH2:11][O:12][CH:13]([F:15])[F:14])[C:9]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:24])(=[O:18])[CH3:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57539234HCID 57539234, compound

Product 1

HCID 23648567HCID 23648567, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-Butyl {(1R)-2-(benzylamino)-1-[(difluoromethoxy)methyl]-2-oxoethyl}carbamate (340 mg, 0.987 mmol) was stirred with trifluoroacetic acid (2.25 mL) and dichloromethane (2.5 mL) in an ice bath for an hour. The reaction mixture was concentrated, stirred with acetic anhydride-pyridine (1:1, 5.8 mL) at room temperature for 30 minutes and then diluted with ethyl acetate, washed with saturated sodium bicarbonate, brine, 0.5N HCl and brine again. The organic layer was dried, concentrated, and triturated with diethyl ether to give (2R)-2-(acetylamino)-N-benzyl-3-(difluoromethoxy)propanamide (230.5 mg, 77.2%) as a white solid. Mp: 186.9° C. 1H NMR (300 MHz, DMSO-d6): (ppm) 8.60 (t, 1H), 8.30 (d, 1H), 7.28-7.45 (m, 5H), 6.67 (wt, 1H), 4.58 (m, 1H), 4.40 (d, 2H), 3.98 (d, 2H) and 1.88 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate, brine, 0.5N HCl and brine again
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-fa0ad3e7c5324f838573e4556aa8c218
Source dataset
uspto-grants-2013_05
Patent number
US08450336B2

Reaction notes

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