Hydrochloric Acid → HCID 22258045, compound

HRID 567894Notes

Reaction equation

HRID 567894 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]([S:25]([CH2:28][CH2:29][CH2:30][C:31]([O:33]C)=[O:32])(=[O:27])=[O:26])=[C:12]([CH2:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)[S:13][C:7]=2[N:6]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:5]1=[O:39].Cl>CO.O1CCCC1.O>[CH3:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]([S:25]([CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])(=[O:27])=[O:26])=[C:12]([CH2:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)[S:13][C:7]=2[N:6]([CH2:35][CH:36]([CH3:37])[CH3:38])[C:5]1=[O:39]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22257962HCID 22257962, compound

Product 1

HCID 22258045HCID 22258045, compoundYield 28.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide solution (1M, 1 ml) 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)sulfonyl]butanoate (0.10 g) in methanol (3 ml) and tetrahydofuran (3 ml). After 4 hours, the reaction mixture was diluted with water (20 ml), acidified with hydrochloric acid (2M) and extracted with ethyl acetate (2×30 ml). The organic extracts were evaporated under reduced pressure. The residue was partitioned between ether (30 ml) and aqueous sodium hydroxide solution (0.1M, 30 ml). The aqueous phase was acidified with hydrochloric acid (2M) and extracted with ethyl acetate (2×30 ml). The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was triturated with ethyl acetate/hexane to give the title compound (0.028 g).

Workup

  1. extractionextracted with ethyl acetate (2×30 ml)
  2. customThe organic extracts were evaporated under reduced pressure
  3. customThe residue was partitioned between ether (30 ml) and aqueous sodium hydroxide solution (0.1M, 30 ml)
  4. extractionextracted with ethyl acetate (2×30 ml)
  5. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was triturated with ethyl acetate/hexane

Sources & evidence

ORD record
ord-25747d07fa5b4daa8c9a90608b355a37
Source dataset
uspto-grants-2001_01
Patent number
US06180635B2

Reaction notes

Loading…