Phenethylamine → HCID 69970982, compound

HRID 1700098Notes

Reaction equation

HRID 1700098 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@H:8]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([C:24]#[N:25])=[N:18][C:19]=3Cl)[O:7][C@@H:6]1[CH2:26][O:27][C:28](=[O:30])[CH3:29])(=[O:3])[CH3:2].C(N(CC)CC)C.[CH2:38]([NH2:46])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(#N)C>[C:1]([O:4][C@H:5]1[C@@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@H:8]([N:14]2[CH:22]=[N:21][C:20]3[C:15]2=[N:16][C:17]([C:24]#[N:25])=[N:18][C:19]=3[NH:46][CH2:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[O:7][C@@H:6]1[CH2:26][O:27][C:28](=[O:30])[CH3:29])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 22948625(2R,3R,4R,5R)-4-(Acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate

Product 1

HCID 69970982HCID 69970982, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(6-chloro-2-cyano-9H-purin-9-yl)tetrahydro-3-furanyl acetate (1.96 g, 4.48 mmol) (Preparation 10) and triethylamine (1.8 g, 17.8 mmol) in acetonitrile (20 ml) was treated with phenethylamine (0.60 g, 4.96 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 2 hours. The solvent was removed under reduced pressure and the residue was partitioned between dichloromethane (75 ml) and water (20 ml). The organic phase was separated and the solvent was removed under reduced pressure. The foam was purified by column chromatography on silica gel eluting with dichloromethane:ethyl acetate (4:1 by volume) to give a product which was then azeotroped with diethyl ether to afford the title compound as a foam (2.05 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between dichloromethane (75 ml) and water (20 ml)
  3. customThe organic phase was separated
  4. customthe solvent was removed under reduced pressure
  5. customThe foam was purified by column chromatography on silica gel eluting with dichloromethane:ethyl acetate (4:1 by volume)
  6. customto give a product which
  7. customwas then azeotroped with diethyl ether

Sources & evidence

ORD record
ord-944e5732a3724fc7b0803572a5011045
Source dataset
uspto-grants-2002_02
Patent number
US06350735B1

Reaction notes

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