Hydrochloric Acid → HCID 68380158, compound

HRID 2178654Notes

Reaction equation

HRID 2178654 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C@@H:8]([NH:10]C(=O)OC(C)(C)C)[CH3:9])=[C:4]([C:20]([F:23])([F:22])[F:21])[CH:3]=1.Cl>CO>[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][CH2:7][C@@H:8]([NH2:10])[CH3:9])=[C:4]([C:20]([F:21])([F:22])[F:23])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70807891HCID 70807891, compound

Product 1

HCID 68380158HCID 68380158, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl {(2S)-1-[4-fluoro-2-(trifluoromethyl)phenoxy]propan-2-yl}carbamate (C6) (1.87 g, 5.54 mmol) in methanol (10 mL) was added a solution of hydrogen chloride (4 N in 1,4-dioxane, 5 mL). After 4 hours, the reaction mixture was concentrated in vacuo. The resulting residue was taken up in dichloromethane and washed with saturated aqueous sodium bicarbonate solution and water. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0 to 20% methanol in ethyl acetate) afforded the title compound as a yellow liquid. Yield: 785 mg, 3.31 mmol, 60%. LCMS m/z 238.1 (M+1). 1H NMR (400 MHz, CDCl3) δ 1.19 (d, J=6.5 Hz, 3H), 3.35-3.44 (m, 1H), 3.74 (dd, J=8.4, 7.4 Hz, 1H), 3.94 (dd, J=8.5, 4.0 Hz, 1H), 6.93 (dd, J=9.1, 4.2 Hz, 1H), 7.18 (br ddd, J=9, 8, 3 Hz, 1H), 7.30 (dd, J=8.4, 3.1 Hz, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. washwashed with saturated aqueous sodium bicarbonate solution and water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via silica gel chromatography (Gradient: 0 to 20% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-e4e6c66e3eac4ff89d5340fc0a2324c5
Source dataset
uspto-grants-2015_06
Patent number
US09067934B2

Reaction notes

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