Hydrochloric Acid → HCID 118045332, compound

HRID 596000Notes

Reaction equation

HRID 596000 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:24]C(=O)OC(C)(C)C)[CH2:10][NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13])[CH:5]=[C:6]([I:8])[CH:7]=1.[C:32]([O-])([O-])=O.[K+].[K+].IC.Cl>CN(C=O)C.O.CCOC(C)=O.C(Cl)Cl.O1CCOCC1>[NH2:24][C@@H:9]([C:4]1[CH:5]=[C:6]([I:8])[CH:7]=[C:2]([F:1])[CH:3]=1)[CH2:10][N:11]([CH3:32])[S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])(=[O:14])=[O:13]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 118054630HCID 118054630, compound

Product 1

HCID 118045332HCID 118045332, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

(S)-tert-butyl (1-(3-fluoro-5-iodophenyl)-2-(2-nitrophenylsulfonamido)ethyl)carbamate (290 mg, 0.513 mmol) was dissolved in DMF (5.1 mL) and K2CO3 (142 mg, 1.026 mmol) followed by iodomethane (48.1 μl, 0.769 mmol) were added. The mixture was agitated at room temperature for 1 h upon which complete reaction observed. RM diluted with water and EtOAc. The organic layer was washed with water twice and dried (magnesium sulfate), filtered and concentrated in vacuo to give relatively pure product which was dissolved in DCM (5 mL) and treated with 4N HCl in dioxane (2 mL) and the mixture agitated at room temperature overnight and the mixture concentrated in vacuo to afford the desired product (S)—N-(2-amino-2-(3-fluoro-5-iodophenyl)ethyl)-N-methyl-2-nitrobenzenesulfonamide as the hydrochloride salt. LCMS (m/z): 480.4 (MH+), 0.72 min.

Workup

  1. additionwere added
  2. washThe organic layer was washed with water twice
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give relatively pure product which
  7. stirringthe mixture agitated at room temperature overnight
  8. concentrationthe mixture concentrated in vacuo

Sources & evidence

ORD record
ord-59a67037c3cc4c05a5e5aa0eee4e6163
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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