(1R)-(-)-10-Camphorsulfonic acid synthesis
- Product Name:(1R)-(-)-10-Camphorsulfonic acid
- CAS Number:35963-20-3
- Molecular formula:C10H16O4S
- Molecular Weight:232.3
137234-71-0
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35963-20-3
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Yield:35963-20-3 93.2%
Reaction Conditions:
Stage #1: (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonatewith potassium carbonate in dichloromethane;water; pH=8.9;
Stage #2: in dichloromethane;cyclohexane at 20 - 50; for 8 h;Reagent/catalyst;
Steps:
4
40 g of voriconazole camphorsulfonate was dissolved in 120 ml of dichloromethane and 180 ml of water, and the pH was adjusted to 8.9 with a saturated potassium carbonate solution.The organic layer was separated, the aqueous layer was extracted twice with 20 ml of dichloromethane, then dichloromethane layer was discarded, and the aqueous layer was acidified with concentrated phosphoric acid to pH value of 1.0.The mixture was evaporated to dryness to give a solid (16.5 g). To the solid, 65 ml of dichloromethane was added and the mixture was heated to 50 ° C to dissolve the solid, filtered, and the filtrate was added to 65 ml of cyclohexane, and the mixture was crystallized at room temperature for 8 hours.After suction filtration, the filter cake was dried at 85-90 ° C to obtain 14.9 g of (R)-10-camphorsulfonic acid.Yield: 93.2%.
References:
CN108276310,2018,A Location in patent:Paragraph 0028-0029; 0034-0035; 0037-0046
82509-30-6
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35963-20-3
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35963-20-3
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5872-08-2
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3144-16-9
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35963-20-3
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7647-01-0
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2935-35-5
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5872-08-2
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3144-16-9
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35963-20-3
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$6.00/25g