Potassium Carbonate → HCID 69885816, compound

HRID 1280677Notes

Reaction equation

HRID 1280677 reaction equation
C1(C)C=CC(S(O[CH2:11][CH:12]2[CH2:16][S:15][C:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[N:13]2)(=O)=O)=CC=1.[SH:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[N:30]1[CH:31]=[CH:32][C:27]([S:26][CH2:11][CH:12]2[CH2:16][S:15][C:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[N:13]2)=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22747841tert-butyl N-[(4RS)-4-(p-toluenesulfonyloxymethyl)-4,5-dihydro-2-thiazolyl]carbamateHCID 178418431pyridine-4-thiol

Product 1

HCID 69885816HCID 69885816, compoundYield 28.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

a suspension of 1.5 g of tert-butyl N-[(4RS)-4-(p-toluenesulphonyl-oxymethyl)-4,5-dihydro-2-thiazolyl]carbamate in 50 cm3 of acetonitrile is heated until the reagent has dissolved and 0.604 g of 4-mercaptopyridine is then added with stirring. After cooling to a temperature in the region of 20° C., 1.07 g of potassium carbonate are added. After stirring for 48 hours at a temperature in the region of 20° C., the reaction mixture is filtered. The filtrate is concentrated under reduced pressure (1 kPa) at a temperature in the region of 50° C. The residue obtained is taken up in ethyl acetate and water and the phases are separated after settling has taken place. The organic phase is washed with sodium chloride solution, dried over magnesium sulphate and chromatographed on a column of alumina, eluting with successive mixtures of ethyl acetate/cyclohexane (50/50 by volume). The fractions containing the expected product are purified by chromatography on a column of silica gel, eluting with ethyl acetate. The fractions containing the expected product are combined and then concentrated under the above conditions. 0.356 g of tert-butyl N-[(4RS)-4-(4-pyridylsulphanylmethyl)-4,5-dihydro-2-thiazolyl]carbamate is obtained in the form of a yellow oil [1H NMR spectrum (300 MHz, (CD3)2SO-d6, δ in ppm): 1.42 (s: 9H); 3.09 (dd, J=11.5 and 6 Hz: 1H); 3.29 (mt: 2H); 3.40 (dd, J=11.5 and 8 Hz: 1H); 4.25 (mt: 1H); 7.35 (dd, J=5 and 1.5 Hz: 2H); 8.40 (dd, J=5 and 1.5 Hz: 2H); from 9.70 to 10.00 (broad unresolved complex: 1H)]

Workup

  1. temperatureis heated until the reagent
  2. dissolutionhas dissolved
  3. additionare added
  4. stirringAfter stirring for 48 hours at a temperature in the region of 20° C.
  5. filtrationthe reaction mixture is filtered
  6. concentrationThe filtrate is concentrated under reduced pressure (1 kPa) at a temperature in the region of 50° C
  7. customThe residue obtained
  8. customwater and the phases are separated after settling
  9. washThe organic phase is washed with sodium chloride solution
  10. dry with materialdried over magnesium sulphate
  11. customchromatographed on a column of alumina
  12. washeluting with successive mixtures of ethyl acetate/cyclohexane (50/50 by volume)
  13. additionThe fractions containing the expected product
  14. customare purified by chromatography on a column of silica gel
  15. washeluting with ethyl acetate
  16. additionThe fractions containing the expected product
  17. concentrationconcentrated under the above conditions

Sources & evidence

ORD record
ord-8b260ec5bd0e47249a1740e59e7e5af5
Source dataset
uspto-grants-2002_09
Patent number
US06451821B1

Reaction notes

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