Phosphoric Acid → Dicyclohexylamine

HRID 1823244Notes

Reaction equation

HRID 1823244 reaction equation
P(=O)(O)(O)O.C([N:10]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14])CCC.Cl[C:20]1C=CC(C([C@@]2(O)[C@](C(=O)C3C=CC(Cl)=CC=3)(O)[C@@H](COC(=O)C3C=CC(Cl)=CC=3)O[C@@H]2Cl)=O)=C[CH:21]=1.[CH2:56](C(C)=O)[CH:57](C)C>>[CH:15]1([NH:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:57][CH2:56]2)[CH2:16][CH2:17][CH2:18][CH2:21][CH2:20]1

Participants

5

Reactant 4

HCID 1004Phosphoric AcidHCID 7622Tributylamine2×HCID 7909Methyl Isobutyl KetoneHCID 86586583HCID 86586583, compound

Product 1

HCID 7582Dicyclohexylamine

Conditions

Temperature
5 °C

Procedure

To a mixture of 3.32 g of orthophosphoric acid in 67 mL of methyl isobutyl ketone were added 2.11 g of tri-n-butylamine and 6.6 g of molecular sieves 4A, and the mixture was cooled to 5° C. with stirring. To the mixture was added 6.66 g of 2,3,5-O-tris(4-chlorobenzoyl)-α-D-ribosyl chloride. After 1 hour, precipitation of crystals initiated and then a thick suspension was provided. After 10 hours, the ratio of α-form/β-form for compound (19) in the reaction suspension was 10:1. To the suspension was added 6.33 g of tri-n-butylamine to dissolve the precipitated crystals and molecular sieves were removed by filtration. The filtrate was washed with 55 mL of water. The organic layer was ice-cooled. To the mixture was added 2.4 g of cyclohexylamine for crystallization with stirring. After 1 hour, the precipitated crystals were collected by filtration and dried in vacuo at room temperature to provide 7.02 g of a dicyclohexylamine salt of compound (21) as a colorless powder (Yield: 73.0%; α-form:β-form =99:1).

Workup

  1. customprecipitation of crystals
  2. customa thick suspension was provided
  3. waitAfter 10 hours
  4. dissolutionto dissolve the precipitated crystals and molecular sieves
  5. customwere removed by filtration
  6. washThe filtrate was washed with 55 mL of water
  7. temperaturecooled
  8. additionTo the mixture was added 2.4 g of cyclohexylamine
  9. customfor crystallization
  10. stirringwith stirring
  11. waitAfter 1 hour
  12. filtrationthe precipitated crystals were collected by filtration
  13. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-a7ba8d46354e4e9ea39392543a3397b1
Source dataset
uspto-grants-2006_05
Patent number
US07038039B2

Reaction notes

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