Anisole → HCID 178459664, compound

HRID 1374428Notes

Reaction equation

HRID 1374428 reaction equation
[NH2:1][C:2]([O:4][CH2:5][C@@H:6]1[CH2:11][C:10]([C:12]2[N:13]=[C:14]([S:17]CC3C=CC(OC)=CC=3)[S:15][CH:16]=2)=[CH:9][CH2:8][N:7]1[C:27]([O:29][CH2:30][CH:31]=[CH2:32])=[O:28])=[O:3].C1(OC)C=CC=CC=1.C(N)(=S)C1C=CN=CC=1>FC(F)(F)C(O)=O>[NH2:1][C:2]([O:4][CH2:5][C@@H:6]1[CH2:11][C:10]([C:12]2[N:13]=[C:14]([SH:17])[S:15][CH:16]=2)=[CH:9][CH2:8][N:7]1[C:27]([O:29][CH2:30][CH:31]=[CH2:32])=[O:28])=[O:3]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 27237884-PyridinecarbothioamideHCID 86592527HCID 86592527, compound

Product 1

HCID 178459664HCID 178459664, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Allyl (2S)-2-{[(aminocarbonyl)oxy]methyl}-4-{2-[(4-methoxybenzyl)sulfanyl]-1,3-thiazol-4-yl}-3,6-dihydro-1(2 H)-pyridinecarboxylate (74.5 mg, 0.16 mmol) and anisole (35 ml, 0.32 mmol) were dissolved in trifluoroacetic acid (6 ml). And then thioisonicotinamide (3 mg) was added to the solution and the mixture was refluxed at 80–90° C. Four hours later the solvent was removed in vacuo. To the residue was added an aqueous 1N NaOH solution to make the solution alkaline. To the solution were added ethyl acetate and hexane, and the solution was separated with a separating funnel. To the aqueous layer was added 6N hydrochloric acid and the solution was separated with a separating funnel by addition of ethyl acetate. The aqueous layer was extracted with ethyl acetate and the organic layer was washed twice with a saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed in vacuo to give allyl (2S)-2-{[(aminocarbonyl)oxy]methyl}-4-(2-mercapto-1,3-thiazol-4-yl)-3,6-dihydro-1(2 H)-pyridinecarboxylate (37.3 mg, 67%).

Workup

  1. temperaturethe mixture was refluxed at 80–90° C
  2. customFour hours later the solvent was removed in vacuo
  3. additionTo the residue was added an aqueous 1N NaOH solution
  4. additionTo the solution were added ethyl acetate and hexane
  5. customthe solution was separated with a separating funnel
  6. additionTo the aqueous layer was added 6N hydrochloric acid
  7. customthe solution was separated with a separating funnel by addition of ethyl acetate
  8. extractionThe aqueous layer was extracted with ethyl acetate
  9. washthe organic layer was washed twice with a saturated aqueous sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-dcef24c107f84b57a4625422b1316af9
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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