Hydrochloric Acid → HCID 57750309, compound

HRID 423113Notes

Reaction equation

HRID 423113 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH:16]C(=O)OC(C)(C)C)[CH2:10][CH2:11][S:12](=[O:15])(=[O:14])[NH2:13])=[CH:5][CH:4]=1>C(Cl)Cl.CO>[NH2:16][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=1)[CH2:10][CH2:11][S:12]([NH2:13])(=[O:14])=[O:15]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57750297Tert-butyl 1-(4-chlorophenyl)-3-sulfamoylpropylcarbamate2×

Product 1

HCID 57750309HCID 57750309, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

Hydrogen chloride (4M in dioxan, 1.0 mL, 4.00 mmol) was added to tert-butyl 1-(4-chlorophenyl)-3-sulfamoylpropylcarbamate (Intermediate 103) (38 mg, 0.11 mmol) in a mixture of DCM (5 mL) and methanol (2 mL) at 22° C. The resulting solution was stirred at 22° C. for 24 hours. The mixture was evaporated to dryness and the residue was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 30% (2M NH3 in MeOH) in DCM and pure fractions were evaporated to dryness to afford 3-amino-3-(4-chlorophenyl)propane-1-sulfonamide (20.00 mg, 73.8%) as a colourless gum.

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue was purified by ion exchange chromatography
  3. washThe desired product was eluted from the column
  4. custompure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-2023fb3122644c908c2ff52f2a230199
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

Loading…