Tert-butyl 1-(4-chlorophenyl)-3-ureidopropylcarbamate → 1-(3-Amino-3-(4-chlorophenyl)propyl)urea

HRID 423119Notes

Reaction equation

HRID 423119 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:15]C(=O)OC(C)(C)C)[CH2:9][CH2:10][NH:11][C:12]([NH2:14])=[O:13])=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[NH2:15][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH2:9][CH2:10][NH:11][C:12]([NH2:14])=[O:13]

Participants

3

Reactant 1

HCID 57750307Tert-butyl 1-(4-chlorophenyl)-3-ureidopropylcarbamate2×

Product 1

HCID 577503841-(3-Amino-3-(4-chlorophenyl)propyl)ureaYield 62.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
20 °C

Procedure

Tert-butyl 1-(4-chlorophenyl)-3-ureidopropylcarbamate (Intermediate 110) (346 mg, 1.06 mmol) was dissolved in TFA (3 mL) and stirred at 20° C. for 2 hours. The reaction was vacuumed to dryness and was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 0.35M NH3/MeOH and pure fractions were evaporated to dryness to afford 1-(3-amino-3-(4-chlorophenyl)propyl)urea (151 mg, 62.8%) as a yellow gum.

Workup

  1. customwas purified by ion exchange chromatography
  2. washThe desired product was eluted from the column
  3. customwere evaporated to dryness

Sources & evidence

ORD record
ord-9ae638b54ba34d049b29e4926f068699
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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