Sodium Hydroxide → HCID 58356323, compound

HRID 244613Notes

Reaction equation

HRID 244613 reaction equation
[CH3:1][CH:2]([C:4]1[S:8][C:7]([CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:6][C:5]=1[C:16]([O:18]CC)=[O:17])[CH3:3].[OH-].[Na+]>CO>[CH3:3][CH:2]([C:4]1[S:8][C:7]([CH2:9][N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)=[N:6][C:5]=1[C:16]([OH:18])=[O:17])[CH3:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58356387HCID 58356387, compound

Product 1

HCID 58356323HCID 58356323, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A solution of ethyl 5-(1-methylethyl)-2-(4-morpholinylmethyl)-1,3-thiazole-4-carboxylate (77 mg) in methanol (5 ml) was treated with 2M sodium hydroxide solution (5 ml) and the mixture stirred at 20° C. for 18 h. The mixture was concentrated in vacuo and the residue taken up in water (3 ml). The pH was adjusted to pH 5-6 using 2M hydrochloric acid solution and extracted with DCM (10 ml), separated by hydrophobic frit and evaporated to give the title compound as a pale yellow gum (33 mg).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with DCM (10 ml)
  3. customseparated by hydrophobic frit
  4. customevaporated

Sources & evidence

ORD record
ord-3ac17c33d8564339a26e38277ecb8270
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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