Hexane → HCID 23144410, compound

HRID 337522Notes

Reaction equation

HRID 337522 reaction equation
Br[C:2]1[S:6][C:5]([N:7]([CH3:15])[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[N:4][C:3]=1[C:16]1[O:17][CH:18]=[CH:19][CH:20]=1.C([Li])CCC.CCCCCC.[CH2:32]([O:34][CH2:35][C:36](N(OC)C)=[O:37])[CH3:33].[Cl-].[NH4+]>C1COCC1>[CH2:32]([O:34][CH2:35][C:36]([C:2]1[S:6][C:5]([N:7]([CH3:15])[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[N:4][C:3]=1[C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)=[O:37])[CH3:33]

Participants

7

Reactant 5

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 23144283HCID 23144283, compoundHCID 23144489HCID 23144489, compoundHCID 178418339Butyllithium

Product 1

HCID 23144410HCID 23144410, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

tert-Butyl N-[5-bromo-4-(2-furyl)thiazol-2-yl]-N-methylcarbamate (1.41 g, 3.93 mmol) obtained in Step 1 was dissolved in THF (19 mL), and a 1.57 mol/L solution of n-butyllithium in n-hexane (2.75 mL, 4.32 mmol) was added thereto in a stream of argon at −78° C., followed by stirring at −78° C. for 15 minutes. 2-Ethoxy-N-methoxy-N-methylacetamide (1.74 g, 11.8 mmol) was added to the reaction mixture, followed by stirring at room temperature for 2 hours. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1) to afford the entitled Compound 623 (550 mg, 38%).

Workup

  1. customat −78° C.
  2. stirringby stirring at room temperature for 2 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away under reduced pressure
  7. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3e3c752297474456b6bb9b92f65f0a44
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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