Hydrochloric Acid → HCID 66894903, compound

HRID 1257531Notes

Reaction equation

HRID 1257531 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:18]=[C:19]([C:21]3[CH2:25][C@@H:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)[O:23][N:22]=3)[CH:20]=2)[C:11]([O:13]C(C)(C)C)=[O:12])=[N:6][CH:7]=1.Cl>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:18]=[C:19]([C:21]3[CH2:25][C@@H:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)[O:23][N:22]=3)[CH:20]=2)[C:11]([OH:13])=[O:12])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66895837tert-Butyl 3-(5-methylpyridin-2-yl)-5-[(5S)-5-pyridin-2-yl-4,5-dihydroisoxazol-3-yl]benzoate

Product 1

HCID 66894903HCID 66894903, compoundYield 123%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(5-methylpyridin-2-yl)-5-[(5S)-5-pyridin-2-yl-4,5-dihydroisoxazol-3-yl]benzoate (18.6 g, 44.8 mmol) in dichloromethane (100 mL) was added hydrogen chloride (4.0 M in dioxane; 56.0 mL, 224 mmol). The reaction mixture was stirred at ambient temperature. After 18 h, the mixture was concentrated. Dichloromethane was added the suspension was filtered. The solid cake was washed with dihchloromethane and dried under reduced pressure gave the hydrochloride salt of the title compound (19.8 g). MS 359.8 (M+1).

Workup

  1. concentrationthe mixture was concentrated
  2. additionDichloromethane was added the suspension
  3. filtrationwas filtered
  4. washThe solid cake was washed with dihchloromethane
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-66111dace820409c820ccf33beb8b5bf
Source dataset
uspto-grants-2013_06
Patent number
US08461185B2

Reaction notes

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