Sodium Bicarbonate → HCID 22257953, compound

HRID 1611016Notes

Reaction equation

HRID 1611016 reaction equation
S([O-])(O[O-])(=O)=[O:2].[K+].[K+].[CH3:9][N:10]1[C:15](=[O:16])[C:14]2[C:17]([S:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[C:18]([CH2:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[S:19][C:13]=2[N:12]([CH2:39][CH:40]([CH3:42])[CH3:41])[C:11]1=[O:43].C(=O)(O)[O-].[Na+]>CO.O1CCCC1.O>[CH3:9][N:10]1[C:15](=[O:16])[C:14]2[C:17]([S:31]([CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[O:2])=[C:18]([CH2:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[S:19][C:13]=2[N:12]([CH2:39][CH:40]([CH3:41])[CH3:42])[C:11]1=[O:43]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 10313463Potassium peroxymonosulphateHCID 22257977HCID 22257977, compound

Product 1

HCID 22257953HCID 22257953, compoundYield 315.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium peroxymonosulfate (0.163 g) was added to a stirred suspension of methyl 4-[(1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxothieno[2,3-d]pyrimidin-5-yl)thio]butanoate (0.246 g) in methanol (3 ml), tetrahydrofuran (3 ml) and water (3 ml). After 1 hour, the reaction mixture was poured into saturated aqueous sodium bicarbonate solution (20 ml) and extracted with ethyl acetate (2×20 ml) The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography eluting with hexane:ethyl acetate (1:1) followed by trituration with ethyl acetate/hexane to give the title compound (0.80 g)

Workup

  1. extractionextracted with ethyl acetate (2×20 ml) The organic extracts
  2. dry with materialwere dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography
  6. washeluting with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-0bca60438a15485d89654e784357e462
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

Loading…