HCID 58618539, compound → HCID 10131507, compound

HRID 1793794Notes

Reaction equation

HRID 1793794 reaction equation
[C:1]([C@@H:3]1[C@@H:10]2[C@@H:6]([O:7]C(C)(C)[O:9]2)[C@H:5]([N:13]2[CH:21]=[N:20][C:19]3[C:14]2=[N:15][CH:16]=[N:17][C:18]=3[NH:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[O:4]1)#[CH:2]>C(O)(=O)C.O>[CH:23]1([NH:22][C:18]2[N:17]=[CH:16][N:15]=[C:14]3[C:19]=2[N:20]=[CH:21][N:13]3[C@H:5]2[C@H:6]([OH:7])[C@H:10]([OH:9])[C@@H:3]([C:1]#[CH:2])[O:4]2)[CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

3

Reactant 1

HCID 58618539HCID 58618539, compound

Product 1

HCID 10131507HCID 10131507, compound

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
75 °C

Procedure

A solution of [9-((1R,2R,4R,5R)-4-ethynyl-7,7-dimethyl-3,6,8-trioxabicyclo[3.3.0]oct-2-yl)purin-6-yl]cyclopentylamine (0.28 g) was dissolved in 20 ml of a mixture of acetic acid:water (80:20) and stirred overnight at 75° C. Solvent was removed under reduced pressure, and the residue purified by preparative TLC, eluting with methanol:methylene chloride (1:8), to yield (4S,2R,3R,5R)-2-[6-(cyclopentylamino)purin-9-yl]-5-ethynyloxolane-3,4-diol, a compound of Formula I.

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue purified by preparative TLC
  3. washeluting with methanol:methylene chloride (1:8)

Sources & evidence

ORD record
ord-cc4cbf8d6a6c491aba97605cfc8840b4
Source dataset
uspto-grants-2006_04
Patent number
US07022681B2

Reaction notes

Loading…