Hydrochloric Acid → 1-(16-Oxoheptadecyl)-3,7-dimethylxanthine

HRID 964555Notes

Reaction equation

HRID 964555 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([CH3:41])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[C:37](=[O:38])[C:36]2[N:35]([CH3:39])[CH:34]=[N:33][C:32]=2[N:31]([CH3:40])[C:29]1=[O:30].C(N(CC)CC)C.Cl>ClCCl>[O:11]=[C:12]([CH3:41])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[C:37](=[O:38])[C:36]2[N:35]([CH3:39])[CH:34]=[N:33][C:32]=2[N:31]([CH3:40])[C:29]1=[O:30]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 232958871-(16-Hydroxyheptadecyl)-3,7-dimethylxanthine

Product 1

HCID 190774341-(16-Oxoheptadecyl)-3,7-dimethylxanthineYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of oxalyl chloride (0.036 ml, 0.41 mmol) in dichloromethane (3 ml) at -78° C. was added dimethylsulfoxide (0.063 ml, 0.82 mmol), and over 5 minutes, 1-(16-hydroxyheptadecyl)-3,7-dimethylxanthine (0.15 g, 0.35 mmol) in dichlorornethane (2 ml). The resulting reaction mixture was stirred at -78° C. for 30 minutes, and after the addition of triethylamine (0.23 ml, 1.64 mmol), was allowed to warm to 25° C. olier 30 minutes. Hydrochloric acid (1.0M, 10 ml) and dichloromethane (5 ml) were added to the warmed reaction mixture. The organic phase was separated and the aqueous phase was washed with dichlorornethane (10 ml). The organic portions were combined, dried over magnesium sulfate and evaporated to obtain a slightly yellow solid. The yellow solid, purified by chromatography (silica, ethyl acetate/hexane) resulted in 0.070 g of 1-(16-oxoheptadecyl)-3,7-dimethylxanthine as a white solid (47% yield).

Workup

  1. customThe resulting reaction mixture
  2. temperatureto warm to 25° C. olier 30 minutes
  3. customThe organic phase was separated
  4. washthe aqueous phase was washed with dichlorornethane (10 ml)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto obtain a slightly yellow solid
  8. customThe yellow solid, purified by chromatography (silica, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2a31c0e748814af1aba98d9ecd346195
Source dataset
uspto-grants-1998_06
Patent number
US05770595

Reaction notes

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