Propargyl bromide → [1-(5-Bromomethyl-isoxazol-3-yl)-3-methyl-butyl]-carbamic acid t-butyl ester

HRID 433673Notes

Reaction equation

HRID 433673 reaction equation
ClN1C(=O)CCC1=O.[C:9]([O:13][C:14](=[O:24])[NH:15][CH:16]([CH:21]=[N:22][OH:23])[CH2:17][CH:18]([CH3:20])[CH3:19])([CH3:12])([CH3:11])[CH3:10].[CH2:25]([Br:28])[C:26]#[CH:27].C(N(CC)CC)C>C(Cl)(Cl)Cl.O.N1C=CC=CC=1>[C:9]([O:13][C:14](=[O:24])[NH:15][CH:16]([C:21]1[CH:27]=[C:26]([CH2:25][Br:28])[O:23][N:22]=1)[CH2:17][CH:18]([CH3:20])[CH3:19])([CH3:11])([CH3:10])[CH3:12]

Participants

8

Reactant 4

HCID 7842Propargyl bromideHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 73685451[1-(Hydroxyimino-methyl)-3-methyl-butyl]-carbamic acid tert-butyl ester

Product 1

HCID 20610322[1-(5-Bromomethyl-isoxazol-3-yl)-3-methyl-butyl]-carbamic acid t-butyl esterYield 43%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6212ChloroformSolvent

Conditions

Temperature
45 °C

Procedure

N-Chlorosuccinimide (5.80 g, 43.4 mmol, 1.00 equivalents), [1-(hydroxyimino-methyl)-3-methyl-butyl]-carbamic acid tert-butyl ester (10.00 g, 43.4 mmol, 1.00 equivalents) and pyridine (0.70 mL) were stirred in chloroform (70 mL) at room temperature for 1 hour. Propargyl bromide (4.83 mL, 54.3 mmol, 1.25 equivalents) was added and the reaction was heated to 45° C. Triethylamine (6.35 mL, 45.6 mmol, 1.05 equivalents) was added dropwise over 20 minutes at 45° C. The reaction was stirred for an additional 1 hour, then it was diluted with water (200 mL) and extracted with dichloromethane (2×200 mL). The combined organic extracts were washed with saturated sodium bicarbonate (2×200 mL) and brine (200 mL). The organic portion was dried over sodium sulfate. Evaporation of the solvent gave a brown residue that was chromatographed by flash chromatography on silica gel to give the title compound as a white solid (6.48 g, 43%). MS (CI) m/z 247.0 (M−99)

Workup

  1. extractionextracted with dichloromethane (2×200 mL)
  2. washThe combined organic extracts were washed with saturated sodium bicarbonate (2×200 mL) and brine (200 mL)
  3. dry with materialThe organic portion was dried over sodium sulfate
  4. customEvaporation of the solvent
  5. customgave a brown residue that
  6. customwas chromatographed by flash chromatography on silica gel

Sources & evidence

ORD record
ord-cd6985321f9141da8ebf61ea026002a0
Source dataset
uspto-grants-2003_12
Patent number
US06667331B2

Reaction notes

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