Hydrochloric Acid → HCID 22258018, compound

HRID 1611015Notes

Reaction equation

HRID 1611015 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]([S:25][CH2:26][CH2:27][CH2:28][C:29]([O:31]C)=[O:30])=[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]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:5]1=[O:37].Cl>CO.O1CCCC1.O>[CH3:3][N:4]1[C:9](=[O:10])[C:8]2[C:11]([S:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[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]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:5]1=[O:37]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22257977HCID 22257977, compound

Product 1

HCID 22258018HCID 22258018, compoundYield 51.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous sodium hydroxide solution (1M, 4 ml) was added to a solution 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 (0.382 g) in methanol (8 ml) and tetrahydrofuran (4 ml). The mixture was stirred at room temperature for 4 hours, diluted with water (50 ml), acidified with hydrochloric acid (2M) and extracted with an ether/ethyl acetate mixture (5:3, 80 ml). The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residual solid was recrystallised from ethyl acetate/hexane to give the title compound (0.19 g).

Workup

  1. extractionextracted with an ether/ethyl acetate mixture (5:3, 80 ml)
  2. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residual solid was recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e7a7a095e9dc44b5942bc855dbb9c160
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

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