Hydrochloric Acid → HCID 22638642, compound

HRID 2416195Notes

Reaction equation

HRID 2416195 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[C:12]([CH2:14][C:15]([O:17]C)=[O:16])[N:13]=2)=[CH:5][CH:4]=1.[Li+].[OH-].Cl>C1COCC1.CO>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[C:12]([CH2:14][C:15]([OH:17])=[O:16])[N:13]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 22638652HCID 22638652, compound

Product 1

HCID 22638642HCID 22638642, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

This material was prepared according to the procedure described for Example 24(b) using methyl 2-[2-(6-methoxy-3-pyridyl)-1,3-thiazol-4-yl]acetate (Step a, 1.1 g, 4.2 mmol) and LiOH (2 N, 7.0 mL) in THF (10 mL) and MeOH (3 mL). The solution was stirred at RT for 18 h, and HCl (aq. 1 N) was added to adjust the reaction mixture to pH ˜2. The solvents were evaporated and the resulting residue was partitioned between EtOAc (75 mL) and H2O (75 mL). The layers were separated and the aqueous layer was extracted again with EtOAc (75 mL). The organic layers were combined, dried (Na2SO4) and concentrated to afford the title compound as a light yellow solid. MS m/z: 251 (M+1). Calc'd for C11H10N2O3S: 250.04.

Workup

  1. customThis material was prepared
  2. customThe solvents were evaporated
  3. customthe resulting residue was partitioned between EtOAc (75 mL) and H2O (75 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted again with EtOAc (75 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-39dfc1c1785c41f8b30dbe8a87a15152
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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