Phosphoric Acid → Dicyclohexylamine

HRID 1823245Notes

Reaction equation

HRID 1823245 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(OC[C@H]2O[C@H](Cl)CC2)=O)=C[CH:21]=1.[C:36](#N)[CH3:37]>>[CH:15]1([NH:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:37][CH2:36]2)[CH2:16][CH2:17][CH2:18][CH2:21][CH2:20]1

Participants

5

Reactant 4

HCID 1004Phosphoric AcidHCID 6342AcetonitrileHCID 7622Tributylamine2×HCID 14827390HCID 14827390, compound

Product 1

HCID 7582Dicyclohexylamine

Conditions

Temperature
5 °C

Procedure

To a mixture of 3.5 g of orthophosphoric acid in 33 mL of acetonitrile were added 2.2 g of tri-n-butylamine and 3.3 g of molecular sieves 4A, and the mixture was cooled to 5° C. with stirring. To the mixture was added 3.28 g of 5-O-(4-chlorobenzoyl)-2,3-dideoxy-α-D-ribosyl chloride. After 1 hour, precipitation of crystals initiated and then a thick suspension was provided. After 20 hours, the ratio of α-form/β-form for compound (23) in the reaction suspension was 10:1. To the suspension was added 6.5 g of tri-n-butylamine to dissolve the precipitated crystals and molecular sieves were removed by filtration. The filtrate was diluted with 70 mL of toluene and then washed with 55 mL of water. The organic layer was ice-cooled. To the mixture was added 2.5 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 4.56 g of a dicyclohexylamine salt of compound (23) as a colorless powder (Yield: 71.5%; α-form:β-form=97:3).

Workup

  1. customprecipitation of crystals
  2. customa thick suspension was provided
  3. waitAfter 20 hours
  4. dissolutionto dissolve the precipitated crystals and molecular sieves
  5. customwere removed by filtration
  6. additionThe filtrate was diluted with 70 mL of toluene
  7. washwashed with 55 mL of water
  8. temperaturecooled
  9. additionTo the mixture was added 2.5 g of cyclohexylamine
  10. customfor crystallization
  11. stirringwith stirring
  12. waitAfter 1 hour
  13. filtrationthe precipitated crystals were collected by filtration
  14. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-7065587a91b74ef5b8b88a579ab90592
Source dataset
uspto-grants-2006_05
Patent number
US07038039B2

Reaction notes

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