Ammonium Chloride → HCID 18393304, compound

HRID 1638185Notes

Reaction equation

HRID 1638185 reaction equation
Br[CH2:2][CH2:3][C:4]([CH3:6])=[CH2:5].[CH:7]([C@H:10]1[CH2:14][O:13][C:12](=[O:15])[N:11]1[C:16](=[O:19])[CH:17]=[CH2:18])([CH3:9])[CH3:8].[NH4+].[Cl-]>C1COCC1>[CH:7]([C@H:10]1[CH2:14][O:13][C:12](=[O:15])[N:11]1[C:16](=[O:19])[CH2:17][CH2:18][CH2:2][CH2:3][C:4]([CH3:6])=[CH2:5])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5495854-Bromo-2-methylbut-1-eneHCID 10954182(4S)-4-propan-2-yl-3-prop-2-enoyl-1,3-oxazolidin-2-one

Product 1

HCID 18393304HCID 18393304, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

47 mg (1.9 mmol) of Mg chips is stirred at room temperature (or while being heated intermittently) in 1.5 ml of absolute THF with 283 mg (1.9 mmol) of 4-bromo-2-methyl-1-butene, until all Mg has gone into solution. This Grignard solution is mixed at -30° C. with a suspension of 197 mg (1.00 mmol) of CuBr--Me2S in 1.5 ml of absolute THF. It is stirred for 30 minutes at this temperature; 117 mg (0.64 mmol) of 20 on 2 ml of absolute THF is added; it is stirred for 16 hours at -10° C. and hydrolyzed with 10 ml of saturated NH4Cl solution. It is extracted three times with 20 ml of Et2O each. After drying on MgSO4, the solvent is removed. By flash-chromatographic purification with pentane/Et2O (15:1), 128 mg (0.51 mmol, 79%) of 21a is obtained.

Workup

  1. extractionIt is extracted three times with 20 ml of Et2O each
  2. customAfter drying on MgSO4
  3. customthe solvent is removed
  4. customBy flash-chromatographic purification with pentane/Et2O (15:1)

Sources & evidence

ORD record
ord-910dfedb71d7438fa1aaed1821350ebf
Source dataset
uspto-grants-2000_03
Patent number
US06043372

Reaction notes

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