Hydrochloric Acid → 4-({[(Benzyloxy)carbonyl](methyl)amino}methyl)benzoic acid

HRID 415175Notes

Reaction equation

HRID 415175 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=1)[CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].Cl>CO>[CH2:1]([O:8][C:9]([N:11]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:22][CH:23]=1)[CH3:12])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66621459Methyl 4-(((benzyloxycarbonyl)(methyl)amino)methyl)benzoate

Product 1

HCID 609780604-({[(Benzyloxy)carbonyl](methyl)amino}methyl)benzoic acidYield 56.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The methyl 4-(((benzyloxycarbonyl)(methyl)amino)methyl)benzoate was dissolved in methanol, then LiOH (0.35 g, 14.7 mmol) was added. The resulting mixture was maintained at room temperature for 2 days. The mixture was adjusted to pH=1˜2 with 2N aqueous hydrochloric acid then extracted with ethyl acetate (50 mL×3). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and condensed under vacuum. The residue was purified by silica gel chromatography (petrol ether:ethyl acetate=10:1) to yield a white solid of 4-(((benzyloxycarbonyl)(methyl)amino)methyl)benzoic acid (1.25 g, 56.8%), LC-MS (ESI) m/z 300 [M+1]+.

Workup

  1. extractionthen extracted with ethyl acetate (50 mL×3)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate and condensed under vacuum
  4. customThe residue was purified by silica gel chromatography (petrol ether:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-470714cfcde14aceaaec46daf5d2fc28
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

Loading…