HCID 67190843, compound → HCID 46875598, compound

HRID 1454322Notes

Reaction equation

HRID 1454322 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9][C@@H:10]1[C@H:17]2[C@@H:13]([O:14]C(C)(C)[O:16]2)[C@H:12]([N:20]2[CH:28]=[N:27][C:26]3[C:21]2=[N:22][CH:23]=[N:24][C:25]=3[NH:29][CH:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)[O:11]1>C(O)(=O)C.O>[CH:30]1([NH:29][C:25]2[N:24]=[CH:23][N:22]=[C:21]3[C:26]=2[N:27]=[CH:28][N:20]3[CH:12]2[C@H:13]([OH:14])[C@H:17]([OH:16])[C@@H:10]([CH2:9][S:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[O:11]2)[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 1

HCID 67190843HCID 67190843, compound

Product 1

HCID 46875598HCID 46875598, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

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. 1H NMR (CDCl3) δ 1.6-2.4 (m, 6H), 3.15-3.25 (m, 2H), 4.1 (bs, 1H), 4.4-4.65 (m, 4H), 6.0 (d, 1H), 6.8 (bs, 1H), 7.05 (m, 2H), 7.2 (m, 1H), 7.4 (m, 1H), 7.8 (s, 1H), 8.25 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-a9e6d2c2f6eb4356ba734907f89ee578
Source dataset
uspto-grants-2009_01
Patent number
US07479485B2

Reaction notes

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