Tetrahydrofuran → HCID 58609916, compound

HRID 408493

Reaction equation

HRID 408493 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[C:6]([N:13]1C=C[S:15][CH:14]1[NH2:18])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1CC=O.[O:30]1CCCC1>>[C:9]([O:8][C:6](=[O:7])[NH:13][C:14]1[S:15][C:2]([CH:3]([OH:30])[CH2:4][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[O:20][CH3:19])=[CH:1][N:18]=1)([CH3:10])([CH3:11])[CH3:12]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 2695482-(2-Methoxyphenyl)acetaldehydeHCID 66545324tert-butyl 2-amino-2H-1,3-thiazole-3-carboxylateHCID 178418339Butyllithium

Product 1

HCID 58609916HCID 58609916, compoundYield 28%

Conditions

Temperature
-78 °C

Procedure

A solution of n-butyl lithium (2.5 M, 250 mL, 0.62 mol) was added to a solution of N-Boc-2-aminothiazole (56 g, 0.28 mol) in anhydrous tetrahydrofuran (500 mL) was added at −78° C. After the addition was completed, the mixture was allowed to stir at −78° C. for one hour. A solution of (2-methoxy-phenyl)-acetaldehyde (36 g, 0.24 mol) in tetrahydrofuran (100 mL) was slowly added to the reaction mixture while maintaining a temperature of −78° C. The mixture was allowed to warm to room temperature and stirred for 15 hours. The reaction was quenched with a saturated aqueous solution of ammonium chloride (1000 mL) and extracted three times with ethyl acetate (400 mL). The combined organic layers were washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, and evaporated to dryness. The crude product was purified by column chromatography to give the pure product (28 g, 0.080 mol, 28%).

Workup

  1. additionwas added at −78° C
  2. additionAfter the addition
  3. temperaturewhile maintaining a temperature of −78° C
  4. temperatureto warm to room temperature
  5. stirringstirred for 15 hours
  6. customThe reaction was quenched with a saturated aqueous solution of ammonium chloride (1000 mL)
  7. extractionextracted three times with ethyl acetate (400 mL)
  8. washThe combined organic layers were washed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over sodium sulfate
  10. customevaporated to dryness
  11. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-6c33cdf1efe14b06bbd2feaa337fc178
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Linked notes

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