Hydrochloric Acid → HCID 90010002, compound

HRID 623375Notes

Reaction equation

HRID 623375 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]([C:5]1[CH:24]=[CH:23][C:8]([O:9][CH2:10]/[C:11](=[CH:21]\[F:22])/[CH2:12][NH:13]C(=O)OC(C)(C)C)=[CH:7][CH:6]=1)=[O:4].FC(F)(F)C(O)=O.[ClH:33]>C(Cl)Cl>[ClH:33].[NH2:13][CH2:12]/[C:11](=[CH:21]/[F:22])/[CH2:10][O:9][C:8]1[CH:23]=[CH:24][C:5]([C:3]([N:2]([CH3:25])[CH3:1])=[O:4])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 118117598HCID 118117598, compound

Product 1

HCID 90010002HCID 90010002, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (Z)-tert-butyl 2-((4-(dimethylcarbarnoyl)-phenoxy)methyl)-3-fluoroallylcarbamate (520.0 mg, 1.48 mmol) in CH2Cl2 (8.0 mL) at room temperature was added trifluoroacetic acid (2.0 mL). The resulting mixture was stirred at room temperature for 30 min. All volatiles were removed in vacuo and the residue was co-evaporated with CH2Cl2 (2×20 mL) to remove trifluoroacetic acid. The resulting oil was taken up in ethyl acetate (3.0 mL) and then ethereal HCl (2.0 M in diethyl ether; 1.0 mL, 2.0 mmol) was added. The precipitate formed was isolated and dried under reduced pressure to afford (Z)-4-(2-(aminomethyl)-3-fluoroallyloxy)-N,N-dimethylbenzamide hydrochloride (301 mg, 71%) as a pale yellow solid; m.p.=135-137° C.; 1H-NMR (300 MHz; MeOD) δ ppm: 3.06 (3H, br s), 3.10 (3H, br s), 3.71 (2H, d, J 3.0 Hz), 4.88 (2H, dd, J 2.8, 0.8 Hz), 7.11 (2H, d, J 8.9 Hz), 7.13 (1H, d, J 80.8 Hz), 7.45 (2H, d, J 8.9 Hz).

Workup

  1. customAll volatiles were removed in vacuo
  2. customto remove trifluoroacetic acid
  3. customThe precipitate formed
  4. customwas isolated
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-716a6551883c4bf493a4b1613ee788e9
Source dataset
uspto-grants-2016_04
Patent number
US09302986B2

Reaction notes

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