Tetrahydrofuran → HCID 178459663, compound

HRID 1374413Notes

Reaction equation

HRID 1374413 reaction equation
[Si]([O:8][CH2:9][C@@H:10]1[CH2:15][C:14]([C:16]2[N:17]=[C:18]([SH:21])[S:19][CH:20]=2)=[CH:13][CH2:12][N:11]1[C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])(C(C)(C)C)(C)C.C1COCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[OH:8][CH2:9][C@@H:10]1[CH2:15][C:14]([C:16]2[N:17]=[C:18]([SH:21])[S:19][CH:20]=2)=[CH:13][CH2:12][N:11]1[C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 521998p-Toluenesulfonic acid monohydrateHCID 178459666HCID 178459666, compound

Product 1

HCID 178459663HCID 178459663, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of allyl (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(2-mercapto-1,3-thiazol-4-yl)-3,6-dihydro-1(2 H)-pyridinecarboxylate (539 mg, 1.30 mmol) in ethanol(40 ml)/THF(3 ml) was added p-toluenesulfonic acid monohydrate (50 ml). Four hours later the solvent was removed in vacuo. The residue was made alkaline by adding an aqueous 1N NaOH solution. To the mixture were added ethyl acetate and hexane, and the mixture was separated with a separating funnel. To the aqueous layer was added 6N hydrochloric acid, and the mixture was separated with a separating funnel. The aqueous layer was extracted with ethyl acetate. The organic layer was washed twice with a saturated aqueous sodium chloride solution, was dried over magnesium sulfate and the organic solvent was removed under reduced pressure to give allyl (2S)-2-(hydroxymethyl)-4-(2-mercapto-1,3-thiazol-4-yl)-3,6-dihydro-1(2 H)-pyridinecarboxylate (218 mg, 55%).

Workup

  1. customFour hours later the solvent was removed in vacuo
  2. additionby adding an aqueous 1N NaOH solution
  3. additionTo the mixture were added ethyl acetate and hexane
  4. customthe mixture was separated with a separating funnel
  5. additionTo the aqueous layer was added 6N hydrochloric acid
  6. customthe mixture was separated with a separating funnel
  7. extractionThe aqueous layer was extracted with ethyl acetate
  8. washThe organic layer was washed twice with a saturated aqueous sodium chloride solution
  9. dry with materialwas dried over magnesium sulfate
  10. customthe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-373a87d2f1e94761a625726ac996d387
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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