Hydrochloric Acid → HCID 73554994, compound

HRID 251324Notes

Reaction equation

HRID 251324 reaction equation
C(OC([NH:8][C:9]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])=O)(C)(C)C.[ClH:22]>O1CCOCC1>[ClH:22].[NH2:8][C:9]1[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid3×HCID 150338862-((tert-Butoxycarbonyl)amino)-5-(trifluoromethyl)benzoic acid

Product 1

HCID 73554994HCID 73554994, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent4×

Procedure

A suspension of 2-(tert-butoxycarbonylamino)-5-(trifluoromethyl)benzoic acid (56.34 g, 185 mmol, see: S. Takagishi, et al., Synlett 1992) in dioxane (100 mL) was treated with the dropwise addition of 4 N hydrochloric acid solution in dioxane (250 mL, 1.0 mol), and the mixture was stirred for 4 h. Analysis by LC/MS indicated that the reaction was not complete, so additional 4 N hydrochloric acid solution in dioxane (250 mL, 1.0 mol) was added, and the mixture was stirred overnight. Analysis by LC/MS indicated that the reaction still contained c. 5% of the starting material, so additional 4 N hydrochloric acid solution in dioxane (100 mL, 0.4 mol) was added, and the mixture was stirred for 4 h. Analysis by LC/MS indicated that the reaction was now complete. The mixture was concentrated in-vacuo, and the residue was stripped 2× from methylene chloride to remove any remaining HCl. The 2-amino-5-(trifluoromethyl)benzoic acid, hydrochloride thus obtained was used immediately in the next step. MS (ES+)=206 (M+H+).

Workup

  1. stirringthe mixture was stirred overnight
  2. customAnalysis by LC/MS indicated that the reaction still contained c
  3. stirringthe mixture was stirred for 4 h
  4. concentrationThe mixture was concentrated in-vacuo
  5. customto remove any remaining HCl

Sources & evidence

ORD record
ord-39f0bcf8bea74444802e54e2a70ea048
Source dataset
uspto-grants-2011_01
Patent number
US07863333B2

Reaction notes

Loading…