Reaction #1458448

ord-d6c77a85029940f982a2dafd1468a767

Reaction equation

CC1(C)O[C@@H]2[C@@H](O1)[C@@H](CSc1ccccc1F)O[C@H]2n1cnc2c(NC3CCCC3)ncnc21
(9-{(4S,1R,2R,5R)-4-[(2-fluorophenylthio)methyl]-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl}purin-6-yl)cyclopentylamine
→
O[C@@H]1[C@@H](CSc2ccccc2F)OC(n2cnc3c(NC4CCCC4)ncnc32)[C@@H]1O
(4S,5S,3R)-2-[6-(cyclopentylamino)purin-9-yl]-5-[(2-fluorophenylthio)methyl]oxolane-3,4-diol

Reactants

—
( 4 )
CC1(C)O[C@@H]2[C@@H](O1)[C@@H](CSc1ccccc1F)O[C@H]2n1cnc2c(NC3CCCC3)ncnc21
(9-{(4S,1R,2R,5R)-4-[(2-fluorophenylthio)methyl]-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl}purin-6-yl)cyclopentylamine

Reagents

None

Solvents

CC(=O)O
acetic acid
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureheated at 90 C for 16 hours
  2. 2
    OtherSolvents were removed under reduced pressure
  3. 3
    Otherthe residue was purified by preparative TLC [methanol-dichloromethane(1:9)]

Procedure

(9-{(4S,1R,2R,5R)-4-[(2-fluorophenylthio)methyl]-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl}purin-6-yl)cyclopentylamine, a compound of formula (4) (50 mg) was dissolved in a mixture of acetic acid (8 mL) and water (2 mL) and heated at 90 C for 16 hours. Solvents were removed under reduced pressure, and the residue was purified by preparative TLC [methanol-dichloromethane(1:9)] to afford (4S,5S,3R)-2-[6-(cyclopentylamino)purin-9-yl]-5-[(2-fluorophenylthio)methyl]oxolane-3,4-diol, a compound of Formula I.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07157440B2uspto-grants-2007_01