2-((tert-Butoxycarbonyl)amino)-5-(trifluoromethyl)benzoic acid → 2-Isopropoxycarbonylamino-5-trifluoromethyl-benzoic acid
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
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 (900 mg) was dissolved in THF (10 mL), water (2 mL), and Et3N (1.8 mL) prior to the addition of 1M i-propyl chloroformate (4.5 mL) in toluene. The reaction was stirred for 4 h 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 CH2Cl2 to give the title compound (800 mg). MS found: (2M−1)−=581.2.
Workup
- concentrationthe solution was concentrated to a white solid
- dissolutionA portion of this material (900 mg) was dissolved in THF (10 mL)
- additionwater (2 mL), and Et3N (1.8 mL) prior to the addition of 1M i-propyl chloroformate (4.5 mL) in toluene
- additionwas added
- washThe EtOAc layer was washed with 1N HCl and brine before it
- customwas dried
- filtrationfiltered
- concentrationconcentrated to a crude material
- customThis material was crystallized with CH2Cl2
Sources & evidence
- ORD record
- ord-9c8013b1e4334c0ea13274b312c754f1
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07087604B2
Reaction notes
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