Hydrochloric Acid → HCID 68774647, compound

HRID 1969324Notes

Reaction equation

HRID 1969324 reaction equation
[CH:1]1([NH:7][C:8]([C:10]2[CH:29]=[CH:28][C:13]([O:14][CH2:15]/[C:16](/[F:27])=[CH:17]\[CH2:18][NH:19]C(=O)OC(C)(C)C)=[CH:12][CH:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[ClH:37]>ClCCl>[ClH:37].[NH2:19][CH2:18]/[CH:17]=[C:16](/[F:27])\[CH2:15][O:14][C:13]1[CH:28]=[CH:29][C:10]([C:8]([NH:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:9])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 59588984HCID 59588984, compound

Product 1

HCID 68774647HCID 68774647, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (E)-tert-butyl 4-(4-(cyclohexyl-carbamoyl)phenoxy)-3-fluorobut-2-enylcarbamate (1.25 g, 3.1 mmol) in dichloromethane (54 mL) was added trifluoroacetic acid (6 mL). The reaction was then stirred at room temperature for 3 hours at which time TLC analysis showed no remaining starting material. Evaporation of the solvent and the remaining acid afforded a brown gum. Aqueous HCl (2 M; 5 mL) was then added and the reaction stirred for 40 minutes, upon which point an off-white solid had precipitated out of solution. Filtered, washing with ice cold aqueous HCl (1 M; 3 mL) and dried in a 60° C. oven to afford the title compound as an off-white powder (0.89 g, 85%); m.p.=210-212° C.; 1H-NMR (400 MHz, (CD3)2SO): δppm: 1.11 (1H, m), 1.15-1.33 (4H, m), 1.59 (1H, m), 1.70-1.77 (4H, m), 3.59 (2H, d, J 8.1 Hz), 3.71 (1H, m), 4.87 (2H, d, J 19.8 Hz), 5.52 (1H, dt, J 18.9, 7.8 Hz), 7.01 (2H, d, J 7.9 Hz), 7.83 (2H, d, J 7.9 Hz), 7.97-8.10 (3H, br s, NHs).

Workup

  1. customEvaporation of the solvent
  2. customthe remaining acid afforded a brown gum
  3. stirringthe reaction stirred for 40 minutes, upon which point an off-white solid
  4. customhad precipitated out of solution
  5. filtrationFiltered
  6. washwashing with ice cold aqueous HCl (1 M; 3 mL)
  7. customdried in a 60° C. oven

Sources & evidence

ORD record
ord-71e960d0dc4c46c496a8d8cd842eca82
Source dataset
uspto-grants-2013_04
Patent number
US08426587B2

Reaction notes

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