Hydrochloric Acid → (R)-2-[(Phenylisopropyl)Amino]Adenosine

HRID 22067Notes

Reaction equation

HRID 22067 reaction equation
[C:1]1([CH:7]([NH:10][C:11]2[N:12]=[C:13]([NH2:29])[C:14]3[N:15]=[CH:16][N:17]([C:27]=3[N:28]=2)[C@@H:18]2[O:26][C@H:23]([CH2:24][OH:25])[C@@H:21]([OH:22])[C@H:19]2[OH:20])[CH2:8]C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:31](=O)(O)[O-].[Na+]>>[C:1]1([C:7]([NH:10][C:11]2[N:12]=[C:13]([NH2:29])[C:14]3[N:15]=[CH:16][N:17]([C:27]=3[N:28]=2)[C@@H:18]2[O:26][C@H:23]([CH2:24][OH:25])[C@@H:21]([OH:22])[C@H:19]2[OH:20])([CH3:8])[CH3:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 53927112(R)-2-[(1-Phenylpropyl)amino]adenosine

Product 1

HCID 54295855(R)-2-[(Phenylisopropyl)Amino]Adenosine

Procedure

Treat the secondary amine (3) (249 mg, 0.57 mmol) with 1M hydrochloric acid (20 ml) and heat the reaction to 50° C. for 30 minutes. Cool the reaction and pour into saturated sodium bicarbonate (200 ml). Extract the reaction with chloroform (3×150 ml). Combine the organic extracts, dry over anhydrous magnesium sulfate, filter, and concentrate under vacuum. Purify the residue by radial chromatography (2% to 4% to 8% to 15% methanol/chloroform, 4 mm plate) four times to provide the title compound (105 mg) as the free base. Treat this with ethereal hydrogen chloride, filter, and dry the solid under high vacuum over phosphorous pentoxide to provide the hydrochloride salt of the Formula I (48 mg), m.p. 153° C. dec.; [α]D20 =30° (c=1.04, H2O)

Workup

  1. temperatureheat
  2. customthe reaction to 50° C. for 30 minutes
  3. temperatureCool
  4. customthe reaction
  5. extractionExtract
  6. customthe reaction with chloroform (3×150 ml)
  7. dry with materialCombine the organic extracts, dry over anhydrous magnesium sulfate
  8. filtrationfilter
  9. concentrationconcentrate under vacuum
  10. customPurify the residue by radial chromatography (2% to 4% to 8% to 15% methanol/chloroform, 4 mm plate) four times

Sources & evidence

ORD record
ord-d58e146c116e4309a5081892b9d2cb0b
Source dataset
uspto-grants-1995_06
Patent number
US05426101

Reaction notes

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