Hydrochloric Acid → HCID 58447828, compound

HRID 592253Notes

Reaction equation

HRID 592253 reaction equation
[S:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([CH:13](C(OCC)=O)[C:14]([O:16]CC)=[O:15])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[S:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 58447952HCID 58447952, compound

Product 1

HCID 58447828HCID 58447828, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
88 °C

Procedure

2-(6-Thiomorpholinopyridin-3-yl)malonate 219-3 (564 mg, 1.67 mmol) was stirred with NaOH (334 mg, 8.35 mmol) in dioxane (5 ml) and water (5 ml) for 4 hours. HCl solution was added to adjust the pH around 1 and the reaction mixture heated at 88° C. for 1 hour. Then Na2CO3 was used to adjust the pH to around 4 before the solvents were evaporated. The residue was extracted with ethyl acetate and the organic extraction dried over Na2SO4 and concentrated by rotary evaporation. Purification with reverse phase HPLC afforded 2-(6-thiomorpholinopyridin-3-yl)acetic acid 219-4.

Workup

  1. customwere evaporated
  2. extractionThe residue was extracted with ethyl acetate
  3. extractionthe organic extraction
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated by rotary evaporation
  6. customPurification with reverse phase HPLC

Sources & evidence

ORD record
ord-92d65d24ed634bf588eba7e094974b5c
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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