Hydrochloric Acid → 3-bromo-5-[(5S)-5-(2-pyridinyl)-4,5-dihydro-3-isoxazolyl]benzoic acid
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([C:15]2[CH2:19][C@@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[O:17][N:16]=2)[CH:14]=1)[C:5]([O:7]C(C)(C)C)=[O:6].Cl>O1CCOCC1.Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([C:15]2[CH2:19][C@@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[O:17][N:16]=2)[CH:14]=1)[C:5]([OH:7])=[O:6]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of tert-butyl 3-bromo-5-[(5S)-5-(2-pyridinyl)-4,5-dihydro-3-isoxazolyl]benzoate (0.530 g, 1.31 mmol) in dioxane (6.5 mL) was added hydrogen chloride (4M in dioxane, 1.3 mL, 5.26 mmol). The reaction mixture was stirred at 50° C. for 2 h. Two drops of concentrated hydrogen chloride (12.1 N) were added. The reaction mixture was stirred at 50° C. for 2 d. The mixture was concentrated to dryness to give the hydrochloride salt of the title compound which was used directly in Step B (0.476 g). MS 346.9 (M+1).
Workup
- stirringThe reaction mixture was stirred at 50° C. for 2 d
- concentrationThe mixture was concentrated to dryness
Sources & evidence
- ORD record
- ord-0d586075e7194cdfbe86e82972b830ae
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08461185B2
Reaction notes
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