Sodium Hydroxide → HCID 18358014, compound

2.1 ml of a 1N aqueous solution of sodium hydroxide were added dropwise to a solution of 218 mg of methyl {3-[4-(1,2-dithiolan-3-yl)butyl]ureido}acetate (prepared as described in Example 46) in 4 ml of methanol, and then the mixture was stirred at room temperature for 5 hours. The reaction mixture was then allowed to stand overnight at room temperature, after which the solvent was removed from the reaction mixture by distillation under reduced pressure. Water was added to the residue. The resulting mixture was neutralized by the addition of 2N aqueous hydrochloric acid, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Ethyl acetate was removed from the extract to distillation under reduced pressure. The residue was recrystallized from a 3:1 by volume mixture of ethyl acetate and hexane, to give 64 mg of the title compound as a pale yellow powder, melting at 95 to 96° C.

1. waitto stand overnight at room temperature
2. customafter which the solvent was removed from the reaction mixture by distillation under reduced pressure
3. additionWater was added to the residue
4. additionThe resulting mixture was neutralized by the addition of 2N aqueous hydrochloric acid
5. extractionafter which it was extracted with ethyl acetate
6. washThe extract was washed with a saturated aqueous solution of sodium chloride
7. dry with materialdried over anhydrous sodium sulfate
8. customEthyl acetate was removed from the
9. extractionextract to distillation under reduced pressure
10. customThe residue was recrystallized from a 3:1 by volume mixture of ethyl acetate and hexane

ORD record

ord-b3cbcedca6a04796a82d9ec042963bcd

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06013663