Tert-Butylamine → HCID 69828755, compound
Reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([C:14]2[O:18][N:17]=[C:16]([CH2:19][O:20]C(=O)C)[CH:15]=2)[O:7][C@H:6]1[N:24]1[CH:32]=[N:31][C:30]2[C:25]1=[N:26][CH:27]=[N:28][C:29]=2Cl)(=O)C.C(N(CC)C(C)C)(C)C.Cl.[OH:44][CH:45]1[CH2:49][CH2:48][CH2:47][CH:46]1[NH2:50].C(N)(C)(C)C>C(O)(C)C.CO>[OH:44][C@H:45]1[CH2:49][CH2:48][CH2:47][C@@H:46]1[NH:50][C:29]1[N:28]=[CH:27][N:26]=[C:25]2[C:30]=1[N:31]=[CH:32][N:24]2[C@H:6]1[C@H:5]([OH:4])[C@H:9]([OH:10])[C@@H:8]([C:14]2[O:18][N:17]=[C:16]([CH2:19][OH:20])[CH:15]=2)[O:7]1Participants
Conditions
- Temperature
- 50 °C
Procedure
To a solution of (2R,3R,4R,5S)-4-(acetyloxy)-5-{3-[(acetyloxy)methyl]isoxazol-5-yl}-2-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3-yl acetate (20 mg) in isopropyl alcohol (2 ml) was added N,N-diisopropylethylamine (0.043 ml) and 2-hydroxycyclopentylamine hydrochloride (11.4 mg). The mixture was stirred at 50° C., under nitrogen for 18 h, cooled and evaporated to dryness in vacuo. The resulting residue was purified by automated preparative HPLC (gradient profile 5%-90% (ii) over 20 min) to give the intermediate triacetoxy protected product. To this residue was added methanol (1 ml) and t-butylamine (0.013 ml) and the mixture was stirred at 0° C. for 3 hours. The solvent evaporated in vacuo to yield title compound as a white solid (5 mg).
Workup
- temperaturecooled
- customevaporated to dryness in vacuo
- customThe resulting residue was purified by automated preparative HPLC (gradient profile 5%-90% (ii) over 20 min)
- customto give the intermediate triacetoxy protected product
- stirringthe mixture was stirred at 0° C. for 3 hours
- customThe solvent evaporated in vacuo
Sources & evidence
- ORD record
- ord-d24127c9f53d42e49d9f2a2b03c2107e
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06492348B1
Reaction notes
Loading…