HCID 178521641, compound → HCID 66696651, compound

HRID 856894Notes

Reaction equation

HRID 856894 reaction equation
[CH2-]C(C)=O.[O:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[NH:14][CH2:15][C@@H:16]1[C@H:20]([OH:21])[C@H:19]([OH:22])[C@H:18]([N:23]2[CH:31]=[N:30][C:29]3[C:24]2=[N:25][CH:26]=[N:27][C:28]=3[CH:32]2[CH2:36][CH2:35][O:34][CH2:33]2)[O:17]1>C(O)(=O)C.O>[O:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[NH:14][CH2:15][C@@H:16]1[C@H:20]([OH:21])[C@H:19]([OH:22])[C@H:18]([N:23]2[CH:31]=[N:30][C:29]3[C:24]2=[N:25][CH:26]=[N:27][C:28]=3[CH:32]2[CH2:36][CH2:35][O:34][CH2:33]2)[O:17]1

Participants

4

Reactant 1

HCID 178521641HCID 178521641, compound

Product 1

HCID 66696651HCID 66696651, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of (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), in 80% acetic acid in water (10 mL) was heated to 80° C. for 16 hours. Solvent was evaporated form the reaction product and the residue was 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 as a white foam. MS (M+1).

Workup

  1. customSolvent was evaporated form the reaction product
  2. customthe residue was purified by preparative TLC (5%MeOH/DCM)

Sources & evidence

ORD record
ord-8db0c19c8bbe43bda09f025968e005c7
Source dataset
uspto-grants-2006_12
Patent number
US07144871B2

Reaction notes

Loading…