Isopropylamine → HCID 69827790, compound

HRID 2297655Notes

Reaction equation

HRID 2297655 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([C:21]([OH:23])=[O:22])[O:12]1.[CH:24]([NH2:27])([CH3:26])[CH3:25]>C(O)(C)C>[CH:24]([NH:27][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@H:11]1[C@@H:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]2[C@@H:13]([C:21]([OH:23])=[O:22])[O:12]1)([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 14374715HCID 14374715, compound

Product 1

HCID 69827790HCID 69827790, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of (3aS,4S,6R,6aR)-6-(6-chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (5.82 g) and isopropyl amine (7.27 ml) in isopropanol (20 ml) was heated under reflux for 40 h, cooled to room temperature and concentrated in vacuo. The resulting residue was partitioned between ethyl acetate (75 ml) and citric acid (0.5M, 75 ml). The layers were separated, and the organic phase washed with citric acid solution (2×50 ml). The combined organic extracts were washed with water (50 ml) and brine (80 ml), dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a light brown foam (4.49 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 40 h
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was partitioned between ethyl acetate (75 ml) and citric acid (0.5M, 75 ml)
  5. customThe layers were separated
  6. washthe organic phase washed with citric acid solution (2×50 ml)
  7. washThe combined organic extracts were washed with water (50 ml) and brine (80 ml)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7794ca86c5eb4b6fad4e8f9c2d13ba2e
Source dataset
uspto-grants-2002_12
Patent number
US06492348B1

Reaction notes

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