Carbamate → 2,2-Dimethoxypropane

HRID 1368853Notes

Reaction equation

HRID 1368853 reaction equation
[C:1](=O)([O-:3])N.C1N=C(Cl)C2N=CN([C@@H:15]3[O:19][C@H:18]([CH2:20]O)[C@@H:17](O)[C@H]3O)C=2N=1.N[C@H]1CCCO1>>[CH2-:17][C:18]([CH3:20])=[O:19].[CH3:1][O:3][C:18]([O:19][CH3:15])([CH3:17])[CH3:20]

Participants

5

Reactant 3

HCID 276CarbamateHCID 930036-Chloropurine ribosideHCID 44140826HCID 44140826, compound

Product 2

HCID 64952,2-DimethoxypropaneHCID 178477758HCID 178477758, compound

Procedure

Preparation of compounds 6 and 7 starting from compound 3 is shown in the synthesis scheme below. Compound 3 was prepared from 6-chloropurineriboside 1 and 3 (R)-aminotetrahydrofuran following the procedure reported earlier (U.S. Pat. No. 5,789,416). Protection of the 2′ and 3′ hydroxy groups as an acetonide with 2,2-dimethoxypropane in the presence of TsOH(cat.) gave 4. Reaction of 4 with CDI in THF followed by treatment with 40% aq.methylamine gave carbamate 5. Deprotection of the 2′,3′ acetonide with 80% AcOH/water at 80-90 C. gave carbamate 6. Esterification of 6 with acetic anhydride in pyridine gave diester 7.

Workup

  1. customis shown in the synthesis scheme below

Sources & evidence

ORD record
ord-8b602decbd3a45758793bba8bf560053
Source dataset
uspto-grants-2003_06
Patent number
US06576620B2

Reaction notes

Loading…