2-Methoxybenzaldehyde → HCID 58609897, compound

HRID 408498

Reaction equation

HRID 408498 reaction equation
C([Li])CCC.[CH2:6]([O:8][C:9]([C:11]1[N:12]=[C:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[S:14][CH:15]=1)=[O:10])[CH3:7].[CH3:24][O:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH:28]=[O:29]>O1CCCC1>[CH2:6]([O:8][C:9]([C:11]1[N:12]=[C:13]([NH:16][C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[S:14][C:15]=1[CH:28]([OH:29])[C:27]1[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=1[O:25][CH3:24])=[O:10])[CH3:7]

Participants

5

Reactant 3

HCID 86582-MethoxybenzaldehydeHCID 22280595Ethyl 2-((tert-butoxycarbonyl)amino)-1,3-thiazole-4-carboxylateHCID 178418339Butyllithium

Product 1

HCID 58609897HCID 58609897, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Butyl lithium (2.5 M, 53 mL, 132 mmol) was slowly added to a solution of 2-tert-butoxycarbonylamino-thiazole-4-carboxylic acid ethyl ester (16.4 g, 60 mmol) in anhydrous tetrahydrofuran (250 mL) at −78° C. under a nitrogen atmosphere. A solution of 2-methoxybenzaldehyde (10.89 g, 79.99 mmol) in tetrahydrofuran (50 mL) was then added dropwise at −78° C. The mixture was warmed slowly to room temperature and stirred for 15 hours. The reaction mixture was quenched with a saturated aqueous solution of ammonium chloride (500 mL). The separated aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and evaporated to dryness. The crude product was then purified by column chromatography to yield the pure product (12 g, 29 mmol, 48%).

Workup

  1. customThe reaction mixture was quenched with a saturated aqueous solution of ammonium chloride (500 mL)
  2. extractionThe separated aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layers were washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude product was then purified by column chromatography

Sources & evidence

ORD record
ord-751f3845f70c4c01b100c125cac34ad4
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Linked notes

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