Sodium Bicarbonate → HCID 59364353, compound

HRID 426053Notes

Reaction equation

HRID 426053 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]([CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH3:28])=[O:26])[C:9](=[O:20])[CH2:10][N:11](C)[C:12](=O)OC(C)(C)C)[CH:5]=[CH:6][CH:7]=1.C(=O)(O)[O-].[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]([CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:26])[O:27][CH3:28])[C:9](=[O:20])[CH2:10][NH:11][CH3:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 59364371HCID 59364371, compound

Product 1

HCID 59364353HCID 59364353, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-butyl 2-((3-chlorophenyl)(3-(methoxycarbonylamino)propyl)amino)-2-oxoethyl(methyl)carbamate (130 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 drop wise to adjust the 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-(N-(3-chlorophenyl)-2-(methylamino)acetamido)propylcarbamate (95 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-a16bf7303822477fbc39f0f92644cb87
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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