Hydrochloric Acid → HCID 21258162, compound

HRID 635207Notes

Reaction equation

HRID 635207 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH3:20])[C:13](=[O:21])[N:12]([CH2:22][CH2:23][C:24]([O:26]C)=[O:25])[C:11]=2[N:10]=[C:9]1[C:28]([CH3:31])([CH3:30])[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[Li+].[OH-].Cl>O>[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH3:20])[C:13](=[O:21])[N:12]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])[C:11]=2[N:10]=[C:9]1[C:28]([CH3:29])([CH3:31])[CH3:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 21258170HCID 21258170, compound

Product 1

HCID 21258162HCID 21258162, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

4.6 g (10.8 mmol) of 7-benzyl-8-(tert.-butyl)-3-(2-methoxycarbonylethyl)-1-n-propyl-xanthine are dissolved 50 ml of tetrahydrofuran and 120 ml of water and 3.24 g of LiOH×H2O are added successively with stirring. After about 16 hours' stirring at ambient temperature, the mixture is cooled to about 5° C. and adjusted to pH 5 with 2N HCl (aq.). The organic solvent is largely distilled off in vacuo and the aqueous phase remaining is extracted twice with 150 ml of dichloromethane. The organic phase is dried over MgSO4 and the solvent is distilled off in vacuo. The crude product remaining is purified by chromatography on silica gel (dichloromethane:methanol 90:10). Yield: 3.1 g (88%), amorphous solid.

Workup

  1. additionare added successively
  2. stirringAfter about 16 hours' stirring at ambient temperature
  3. distillationThe organic solvent is largely distilled off in vacuo
  4. extractionthe aqueous phase remaining is extracted twice with 150 ml of dichloromethane
  5. dry with materialThe organic phase is dried over MgSO4
  6. distillationthe solvent is distilled off in vacuo
  7. customThe crude product remaining is purified by chromatography on silica gel (dichloromethane:methanol 90:10)

Sources & evidence

ORD record
ord-220995ad001d491aaf6c9c599d67e47d
Source dataset
uspto-grants-2001_02
Patent number
US06187780B1

Reaction notes

Loading…