Hydrochloric Acid → HCID 11638190, compound

HRID 1814944Notes

Reaction equation

HRID 1814944 reaction equation
C(OC[N:5]1[C:13]2[C:12](=[O:14])[N:11]([CH2:15][CH2:16][CH2:17][CH2:18][C@H:19]([OH:21])[CH3:20])[C:10](=[O:22])[N:9]([CH3:23])[C:8]=2[N:7]=[C:6]1[S:24][CH3:25])C.Cl>C(O)C>[OH:21][C@H:19]([CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15][N:11]1[C:12](=[O:14])[C:13]2[NH:5][C:6]([S:24][CH3:25])=[N:7][C:8]=2[N:9]([CH3:23])[C:10]1=[O:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54139417HCID 54139417, compound

Product 1

HCID 11638190HCID 11638190, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (R)-7-ethoxymethyl-1-(5-hydroxyhexyl)-3-methyl-8-methylsulfanylxanthine (20 mg, 0.054 mmol) in ethanol (1.9 ml) was added concentrated hydrochloric acid (0.10 ml). The reaction mixture was stirred at 80° C. for 24 hours. After evaporation of the solvent under reduced pressure, the crude product was purified by flash chromatography on silica gel eluting with ethyl acetate-methanol (7:1) to provide (R)-1-(5-hydroxyhexyl)-3-methyl-8-methylsulfanylxanthine (12 mg, 70% yield) as a white solid.

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. customthe crude product was purified by flash chromatography on silica gel eluting with ethyl acetate-methanol (7:1)

Sources & evidence

ORD record
ord-82140a030a68486382a9abe5e1a7e652
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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