Hydrochloric Acid → HCID 90009930, compound

HRID 623376Notes

Reaction equation

HRID 623376 reaction equation
[CH3:1][N:2]([CH3:26])[S:3]([C:6]1[CH:25]=[CH:24][C:9]([O:10][CH2:11]/[C:12](=[CH:22]\[F:23])/[CH2:13][NH:14]C(=O)OC(C)(C)C)=[CH:8][CH:7]=1)(=[O:5])=[O:4].FC(F)(F)C(O)=O.[ClH:34]>C(Cl)Cl>[ClH:34].[NH2:14][CH2:13]/[C:12](=[CH:22]/[F:23])/[CH2:11][O:10][C:9]1[CH:8]=[CH:7][C:6]([S:3]([N:2]([CH3:1])[CH3:26])(=[O:5])=[O:4])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 118117823HCID 118117823, compound

Product 1

HCID 90009930HCID 90009930, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of (Z)-tert-butyl 2-((4-(N,N-dimethylsulfamoyl)phenoxy)methyl)-3-fluoroallylcarbamate (279.0 mg, 0.72 mmol) in CH2Cl2 (4.0 mL) at room temperature was added trifluoroacetic acid (1.0 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). The resulting oil was taken up in ethyl acetate/MeOH (5:1; 3.0 mL) and then ethereal HCl (2.0 M in diethyl ether; 0.5 mL, 1.0 mmol) was added. The precipitate formed was isolated and dried under reduced pressure to afford (Z)-4-(2-(aminomethyl)-3-fluoroallyloxy)-N,N-dimethylbenzenesulfonamide hydrochloride (196.0 mg, 84%) as a white solid; m.p. 185-187° C.; 1H-NMR (300 MHz; d6-DMSO) δ ppm: 3.39 (6H, br s), 3.54 (2H, br s), 4.81 (2H, d, J 2.3 Hz), 7.16 (2H, d, J 9.0 Hz), 7.24 (1H, d, J 82.3 Hz), 7.25 (2H, br s), 7.77 (2H, d, J 9.0 Hz).

Workup

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

Sources & evidence

ORD record
ord-5f485717bab5482b9cc6357697885a17
Source dataset
uspto-grants-2016_04
Patent number
US09302986B2

Reaction notes

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