Hydrochloric Acid → HCID 67259494, compound

HRID 1476663Notes

Reaction equation

HRID 1476663 reaction equation
[CH2:1]([O:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][C:11]2[C:10]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=3)=[N:9][C@@H:8]3[CH2:26][CH2:27][S:28](=[O:31])(=[O:30])[CH2:29][C@@H:7]3[C:6]=2[CH:5]=1)[CH3:2].[OH-].[Na+].Cl>O1CCOCC1>[CH2:1]([O:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][C:11]2[C:10]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=3)=[N:9][C@@H:8]3[CH2:26][CH2:27][S:28](=[O:30])(=[O:31])[CH2:29][C@@H:7]3[C:6]=2[CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67257612HCID 67257612, compound2×

Product 1

HCID 67259494HCID 67259494, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 4-[(4aR,10bR)-9-ethoxy-8-methoxy-2,2-dioxido-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoate (380 mg; compound C5) in 1,4-dioxane (10 ml) is treated with an 2 M aqueous solution of sodium hydroxide (1 ml) and the reaction solution is stirred for about 20 h at 45° C. to 50° C. The solution is allowed to come to RT and afterwards a 2 M aqueous solution of hydrogen chloride (1 ml) is added. The mixture is stirred for 20 min at RT, filtered and the filtrate is evaporated to dryness in vacuo. Subsequently, the residue is treated with DCM (30 ml) and the resulting suspension is filtered. The solvent is removed in vacuo to yield the title compound as a solid.

Workup

  1. customto come to RT
  2. stirringThe mixture is stirred for 20 min at RT
  3. filtrationfiltered
  4. customthe filtrate is evaporated to dryness in vacuo
  5. additionSubsequently, the residue is treated with DCM (30 ml)
  6. filtrationthe resulting suspension is filtered
  7. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-eca98a8b7fda4baab1d2110544905150
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

Loading…