Ethanol → HCID 178521641, compound

HRID 856893Notes

Reaction equation

HRID 856893 reaction equation
[CH2-:1][C:2]([CH3:4])=[O:3].[NH2:5][CH2:6][C@@H:7]1[C@H:11]([OH:12])[C@H:10]([OH:13])[C@H:9]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][CH:17]=[N:18][C:19]=3[CH:23]2[CH2:27][CH2:26][O:25][CH2:24]2)[O:8]1.C([N:30]([CH2:33]C)[CH2:31][CH3:32])C.[CH2:35]([OH:37])[CH3:36]>>[CH2-:1][C:2]([CH3:4])=[O:3].[O:37]1[C:35]2[CH:36]=[CH:1][CH:2]=[CH:32][C:31]=2[N:30]=[C:33]1[NH:5][CH2:6][C@@H:7]1[C@H:11]([OH:12])[C@H:10]([OH:13])[C@H:9]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][CH:17]=[N:18][C:19]=3[CH:23]2[CH2:27][CH2:26][O:25][CH2:24]2)[O:8]1

Participants

4

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 178511303HCID 178511303, compound

Product 1

HCID 178521641HCID 178521641, compound

Procedure

To a solution of (4S,2R,3R,5R)-2-aminomethyl-5-[6-(tetrahydrofuran-3-yl)-purin-9-yl]-tetrahydrofuran-3,4-diol acetonide, a compound of formula (11) (100 mg), in ethanol (5 mL) was added triethylamine and 2-chlorobenoxazole, and the mixture was refluxed for 16 hours. The solvent was evaporated and the residue purified by preparative TLC (5%MeOH/DCM) to give (4S,2R,3R,5R)-2-(benzoxazol-2-ylaminomethyl)-5-[6-(tetrahydrofuran-3-yl)-purin-9-yl]-tetrahydrofuran-3,4-diol acetonide, a compound of formula (12).

Workup

  1. temperature2-chlorobenoxazole, and the mixture was refluxed for 16 hours
  2. customThe solvent was evaporated
  3. customthe residue purified by preparative TLC (5%MeOH/DCM)

Sources & evidence

ORD record
ord-e3c01661bc7d45d498168c1c45ec30fe
Source dataset
uspto-grants-2006_12
Patent number
US07144871B2

Reaction notes

Loading…