Water → HCID 86667485, compound

HRID 2401911Notes

Reaction equation

HRID 2401911 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[N:8]=[C:9]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[Se:10][C:11]=2[C:12]([O:14]CC)=[O:13])=[CH:4][CH:3]=1.[OH-].[Li+].O>C(O)(=O)C.O1CCCC1.CO>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[N:8]=[C:9]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[Se:10][C:11]=2[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 962Water2×HCID 3939Lithium Hydroxide2×HCID 56832870HCID 56832870, compound

Product 1

HCID 86667485HCID 86667485, compoundYield 89.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

The ethyl 4-(4-chlorobenzyl)-2-(morpholin-4-yl)-1,3-selenazole-5-carboxylate (35.0 mg, 0.0846 mmol) was placed in a round bottomed flask equipped with a stirbar. Tetrahydrofuran (1.00 mL) and methanol (0.1 mL) were added and the mixture was stirred to give a light yellow solution. A solution of lithium hydroxide in water (2.0 M, 0.423 mL, 0.846 mmol) was added in a single portion, and the resulting mixture was stirred under an atmosphere of nitrogen at room temperature overnight. LCMS analysis of the reaction indicated that starting material still remained; only a small amount of it had been hydrolyzed to the product. Additional tetrahydrofuran (2 mL) and lithium hydroxide in water (2.0 M, 0.423 mL, 0.846 mmol) were added and the reaction was heated overnight at 50° C. under an atmosphere of nitrogen. LCMS analysis indicated that the reaction was 90% complete. The reaction was heated at 60° C. for a further 8 hours. LCMS analysis indicated complete hydrolysis. The reaction was cooled to room temperature, diluted with 10 ml saline, and acidified with dilute acetic acid with good stirring. A white precipitate formed which became granular with stirring. The product was isolated on a flitted funnel, washed with water, and dried at 40° C. overnight to yield 29.2 mg (89% yield) product as a white powder. LC/MS (FA) ES+ 385/387/389. 1H NMR (400 MHz, DMSO) δ 12.73-12.44 (br s, 1H), 7.36-7.24 (m, 4H), 4.26-4.18 (s, 2H), 3.74-3.63 (t, J=4.8 Hz, 4H), 3.49-3.39 (t, J=4.7 Hz, 4H).

Workup

  1. customequipped with a stirbar
  2. customto give a light yellow solution
  3. stirringthe resulting mixture was stirred under an atmosphere of nitrogen at room temperature overnight
  4. temperatureThe reaction was heated at 60° C. for a further 8 hours
  5. customhydrolysis
  6. temperatureThe reaction was cooled to room temperature
  7. additiondiluted with 10 ml saline
  8. customA white precipitate formed which
  9. stirringwith stirring
  10. customThe product was isolated on a flitted funnel
  11. washwashed with water
  12. customdried at 40° C. overnight

Sources & evidence

ORD record
ord-8232860c9cf54e3aa911c1913c1fb68a
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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