Hydrochloric Acid → 3-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid

HRID 1476665Notes

Reaction equation

HRID 1476665 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:17]=[C:18]([CH:23]=[CH:24][CH:25]=3)[C:19]([O:21]C)=[O:20])=[N:9][C@@H:8]3[CH2:26][CH2:27][S:28][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:17]=[C:18]([CH:23]=[CH:24][CH:25]=3)[C:19]([OH:21])=[O:20])=[N:9][C@@H:8]3[CH2:26][CH2:27][S:28][CH2:29][C@@H:7]3[C:6]=2[CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67258949HCID 67258949, compound2×

Product 1

HCID 672606663-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 3-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoate (0.5 g; compound C7) in 1,4-dioxane (8 ml) is added an 2 M aqueous solution of sodium hydroxide (1.3 ml) and the reaction mixture is stirred at RT for 12 h. An aqueous solution of hydrogen chloride (1.3 ml, 2.0 M) is added under stirring. The reaction mixture is evaporated to dryness in vacuo and the resulting residue is used for the next step without further purification.

Workup

  1. stirringunder stirring
  2. customThe reaction mixture is evaporated to dryness in vacuo
  3. customthe resulting residue is used for the next step without further purification

Sources & evidence

ORD record
ord-8cee891cbf484e508b9ac2a0758a8b9a
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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