Hydrochloric Acid → HCID 18187923, compound

HRID 1357829Notes

Reaction equation

HRID 1357829 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([CH2:11][C:12]([CH3:15])([SH:14])[CH3:13])[CH2:7][CH2:6]2)[O:4]CC1.Cl.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH3:15][C:12]([SH:14])([CH3:13])[CH2:11][N:8]1[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 15448993HCID 15448993, compound

Product 1

HCID 18187923HCID 18187923, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of the 1-(8-aza-1,4-dioxaspiro[4.5]dec-8-yl)-2-methylpropane-2-thiol (Synthesis, 1999, 7, 1106) (1.15 g, 4.98 mmol) in THF (12 mL) was added 6 N HCl (12 mL). The mixture was heated at 70° C. overnight, then poured into saturated Na2CO3. The mixture was extracted with EtOAc. The combined organic extracts were dried over Na2SO4 and evaporated. The residue was dissolved in EtOAc and acidified by adding HCl/EtOAc until no more solid formed. The solvent was decanted and the solid was then partitioned between EtOAc and satd Na2CO3. The aqueous layer was extracted with EtOAc and the combined organic extracts were dried over Na2SO4 and evaporated to give the title compound (0.90 g, 4.81 mmol, 97%) as a green oil. 1H NMR (300 MHz, CDCl3) δ 2.96 (t, J=6.0, 4H), 2.52 (s, 2H), 2.41 (t, J=6.0, 4H), 1.34 (s, 6H).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. customevaporated
  4. dissolutionThe residue was dissolved in EtOAc
  5. additionby adding HCl/EtOAc until no more solid
  6. customformed
  7. customThe solvent was decanted
  8. customthe solid was then partitioned between EtOAc
  9. extractionThe aqueous layer was extracted with EtOAc
  10. dry with materialthe combined organic extracts were dried over Na2SO4
  11. customevaporated

Sources & evidence

ORD record
ord-9e7647ff96d44e8cae1e17af964622c0
Source dataset
uspto-grants-2003_07
Patent number
US06593347B2

Reaction notes

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