Hydrochloric Acid → 2-Methoxy-N-[(R)-1-phenoxy-2-propyl]adenosine

HRID 1379644Notes

Reaction equation

HRID 1379644 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:20][C@H:21]([CH3:30])[CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[OH-:31].[Na+].Cl.[CH3:34]O>>[CH3:34][O:31][C:2]1[N:3]=[C:4]([NH:20][C@H:21]([CH3:30])[CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 9845859(2R,3R,4S,5R)-2-[2-Chloro-6-((R)-1-methyl-2-phenoxy-ethylamino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol

Product 1

HCID 228772242-Methoxy-N-[(R)-1-phenoxy-2-propyl]adenosine

Procedure

2-Methoxy- N-[(R)-1-phenoxy-2-propyl]adenosine was prepared by reacting 2-chloro- N-((R)1-phenoxy-2-propyl)adenosine (Example 2)(0.30 g, 0.69 mmol) with a mixture of sodium hydroxide (0.32 g, 8.0 mmol) and methanol (15 ml) in a sealed vessel at 80°-90° C. for 4 h. The cooled reaction mixture was neutralised with concentrated hydrochloric acid and evaporated to dryness. Water (30 ml) was added and the mixture was extracted with dichloromethane (2×30 ml). The combined extracts were dried (MgSO4) and coevaporated with dichloromethane (30 ml), giving the title compound as a foam (0.19 g, 60%), 1H NMR (DMSO-d6)δ 1.32 (3H, d, --CHC H3), 3.55 (1H, m, H-5'a), 3.65 (1H, m, H5'b), 3.72 (3H, s, --CH3), 3.91-3.99 and 4.10-4.20 (4H, 2 m, H-3', H-4' and --CH2 --), 4.51 (1H, dd, H-2'), 4.67 (1H, m, --C HCH3), 5.84 (1H, d, H-1'), 6.89-6.98 (3H, m, Ar--H), 7.26 (2H, dd, Ar--H) 8.12 (1H, br, --NH), 8.46 (1H, s, H-8).

Workup

  1. customThe cooled reaction mixture
  2. customevaporated to dryness
  3. additionWater (30 ml) was added
  4. extractionthe mixture was extracted with dichloromethane (2×30 ml)
  5. dry with materialThe combined extracts were dried (MgSO4)

Sources & evidence

ORD record
ord-d615fe7e71f646299e182d1343e4b440
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

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