Trifluoroacetic acid → Methyl 5-tert-butoxycarbonylaminomethyl-2-nitrobenzoate

HRID 453016Notes

Reaction equation

HRID 453016 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[C:8]([CH2:10][N:11](C(OC(C)(C)C)=O)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:7]=[CH:6][C:5]=1[N+:26]([O-:28])=[O:27].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[C:8]([CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH:7]=[CH:6][C:5]=1[N+:26]([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 687297825-(Di-tert-butoxycarbonylamino-methyl)-2-nitro-benzoic acid methyl ester

Product 1

HCID 19698365Methyl 5-tert-butoxycarbonylaminomethyl-2-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred brown solution of 5-(di-tert-butoxycarbonylamino-methyl)-2-nitro-benzoic acid methyl ester (74.18 g, 180.7 mmol) in methylene chloride (700 mL) was added trifluoroacetic acid (26.2 mL, 352.4 mmol), and the mixture was stirred at room temp overnight. Sat. sodium bicarbonate (400 mL) was added to the solution, and the mixture was stirred for 10 minutes. The organic layer was separated, dried over magnesium sulfate, and evaporated to give 5-(tert-butoxycarbonylamino-methyl)-2-nitro-benzoic acid methyl ester as a brown oil (52.5 g, 94% crude yield). The product was used in the next step without further purification.

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-93432ae3b1d148c2afef54d70e2f4557
Source dataset
uspto-grants-2013_07
Patent number
US08492395B2

Reaction notes

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