Phosphate → HCID 19352564, compound

HRID 378184Notes

Reaction equation

HRID 378184 reaction equation
[CH2:1]([O:9][C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[CH2:24][CH2:25][CH2:26][CH:27]([O:29]C(=O)C)[CH3:28])=[CH:18][CH:17]=2)=[N:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].P([O-])([O-])([O-])=O>C(Cl)(Cl)Cl>[CH2:1]([O:9][C:10]1[CH:15]=[N:14][C:13]([C:16]2[CH:17]=[CH:18][C:19](/[CH:22]=[CH:23]/[CH2:24][CH2:25][CH2:26][CH:27]([OH:29])[CH3:28])=[CH:20][CH:21]=2)=[N:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 1061PhosphateHCID 19352637HCID 19352637, compound

Product 1

HCID 19352564HCID 19352564, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
32.5 °C

Procedure

A mixture of 4.5 g (10 mmol) of the 5-octyloxy-2-{4-(6-acetoxy-1-trans-heptenyl)-phenyl}-pyrimidine, 140 ml of 0.3 M phosphate buffer solution (pH 7.0), 2 ml of chloroform and 0.5 g of Genus Pseudomonas lipase was stirred at 30-35° C. for 40 hours. The mixture was then extracted with 100 ml of toluene, and the organic layer was washed with water and concentrated under reduced pressure. Separation of the residue thus obtained by silica gel column chromatography gave 1.8 g (yield 46%) of (-)-5-octyloxy-2-{4-(6-hydroxy-1-trans-heptenyl)-phenyl}pyrimidine ([α]D20 =-1.2 (c=1.0, CHCl3)) and 2.3 g (yield 53%) of (-)-5-octyloxy-2-{(4-(6-acetoxy-1-trans-heptenyl)-phenyl}-pyrimidine.

Workup

  1. extractionThe mixture was then extracted with 100 ml of toluene
  2. washthe organic layer was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customSeparation of the residue
  5. customthus obtained by silica gel column chromatography

Sources & evidence

ORD record
ord-b8116cd04d7849728409d77c3419ada7
Source dataset
uspto-grants-2000_02
Patent number
US06030546

Reaction notes

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