4-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid → Methyl 4-((((1,1-dimethylethoxy)carbonyl)amino)methyl)benzoate

HRID 565007Notes

Reaction equation

HRID 565007 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:20](N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.CO>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:20])=[O:15])=[CH:17][CH:18]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8536054-(((tert-Butoxycarbonyl)amino)methyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 14221817Methyl 4-((((1,1-dimethylethoxy)carbonyl)amino)methyl)benzoateYield 83.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Procedure

A mixture of 16.2 g (64.5 mmol) of 4-(tert-butoxycarbonylaminomethyl)benzoic acid, 13.6 g (70.9 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1.00 g of 4-dimethylaminopyridine and 200 ml of methanol was stirred at room temperature for 4 hours. Methanol was distilled off under reduced pressure and ice water was poured to the residue thus obtained. The mixture was extracted twice with ethyl acetate and the extract was washed with 10% citric acid aqueous solution and then with saturated sodium hydrogencarbonate aqueous solution and finally with saturated sodium chloride aqueous solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to give 14.3 g (83.6%) of methyl 4-(tert-butoxycarbonylaminomethyl)benzoate.

Workup

  1. distillationMethanol was distilled off under reduced pressure and ice water
  2. additionwas poured to the residue
  3. customthus obtained
  4. extractionThe mixture was extracted twice with ethyl acetate
  5. washthe extract was washed with 10% citric acid aqueous solution
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-97d7ad3f91f14a2c97b4859c91a06906
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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