Sodium Bicarbonate → HCID 66704596, compound

HRID 426058Notes

Reaction equation

HRID 426058 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH2:6][CH2:7][CH2:8][N:9]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)[CH2:10][CH2:11][N:12](C)[C:13](=O)OC(C)(C)C)=[O:4].C(=O)(O)[O-].[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:27][C:23]1[CH:22]=[C:21]([N:9]([CH2:10][CH2:11][NH:12][CH3:13])[CH2:8][CH2:7][CH2:6][NH:5][C:3](=[O:4])[O:2][CH3:1])[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 66704595HCID 66704595, compound

Product 1

HCID 66704596HCID 66704596, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-butyl 2-((3-(methoxycarbonylamino)propyl)(3-chlorophenyl)amino)ethyl(methyl)carbamate (50 mg, 0.31 mmol) was dissolved in a solution of 20% (V/V) TFA/CH2Cl2 (4 mL). The reaction mixture was stirred at room temperature for 1 h, a solution of saturated sodium bicarbonate was added dropwise to adjust pH=7-8. The resulting mixture was extracted with CH2Cl2 (3×10 mL), washed with brine, dried over Na2SO4, concentrated in vacuo to afford methyl 3-((3-chlorophenyl)(2-(methylamino)ethyl)amino)propylcarbamate (40 mg, 95%).

Workup

  1. extractionThe resulting mixture was extracted with CH2Cl2 (3×10 mL)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1174d6069d2e4c7a98af482672ad4dec
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

Loading…