2-((tert-Butoxycarbonyl)amino)-5-(trifluoromethyl)benzoic acid → 2-Isopropoxycarbonylamino-5-trifluoromethyl-benzoic acid

HRID 7674Notes

Reaction equation

HRID 7674 reaction equation
[C:1]([O:5][C:6]([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:7])(C)([CH3:3])[CH3:2]>Cl.O1CCOCC1>[CH:1]([O:5][C:6]([NH: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])=[O:7])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 150338862-((tert-Butoxycarbonyl)amino)-5-(trifluoromethyl)benzoic acid

Product 1

HCID 219911232-Isopropoxycarbonylamino-5-trifluoromethyl-benzoic acidYield 5.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(tert-Butoxycarbonyl)amino-5-trifluoromethylbenzoic acid (6.0 g) was dissolved in 4M HCl (4 mL) in dioxane. After 3 h, the solution was concentrated to a white solid. A portion of this material (200 mg) was dissolved in THF (2.5 mL) and 2M K2CO3 (1.46 mL) was added followed by cyclohexanecarbonyl chloride (0.2 mL). The reaction was stirred for 10 min before EtOAc was added. The EtOAc layer was washed with 1N HCl and brine before it was dried, filtered, and concentrated to a crude material. This material was crystallized with CH3CN to give the title compound (302 mg). MS found: (2M−1)−=629.2.

Workup

  1. concentrationthe solution was concentrated to a white solid
  2. dissolutionA portion of this material (200 mg) was dissolved in THF (2.5 mL)
  3. addition2M K2CO3 (1.46 mL) was added
  4. additionwas added
  5. washThe EtOAc layer was washed with 1N HCl and brine before it
  6. customwas dried
  7. filtrationfiltered
  8. concentrationconcentrated to a crude material
  9. customThis material was crystallized with CH3CN

Sources & evidence

ORD record
ord-5512a38e6e4242e797c233f92c35932b
Source dataset
uspto-grants-2006_08
Patent number
US07087604B2

Reaction notes

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