Pivaloyl chloride → 1-(1-Naphthalen-1-yl-ethyl)-aziridine-2-carboxylic acid but-3-enyl-phenethyl-amide

HRID 29056

Reaction equation

HRID 29056 reaction equation
CO[C:3]([CH:5]1[CH2:7][N:6]1[CH:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[CH3:9])=[O:4].O([Si](C)(C)C)[K].CC(C)(C)C(Cl)=O.[CH2:33]([NH:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:34][CH:35]=[CH2:36].C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:33]([N:37]([CH2:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:3]([CH:5]1[CH2:7][N:6]1[CH:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[CH3:9])=[O:4])[CH2:34][CH:35]=[CH2:36]

Participants

7

Reactant 5

HCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 16720109N-(2-phenylethyl)but-3-en-1-amineHCID 866010811-(1-Naphthalen-1-yl-ethyl)-aziridine-2-carboxylic acid methyl esterHCID 178504318HCID 178504318, compound

Product 1

HCID 866010821-(1-Naphthalen-1-yl-ethyl)-aziridine-2-carboxylic acid but-3-enyl-phenethyl-amideYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1 (12.6 g, 49.75 mmol) in THF (200 mL) is added KOTMS (6.38 g, 49.75 mmol). The mixture is stirred overnight at room temperature. The mixture is concentrated and the residue dissolved in dichloromethane (200 mL) and cooled to 0° C. Trimethylacetyl chloride (5.94 g, 49.25 mmol) is added slowly and the mixture is warmed to room temperature over 2 hours. The mixture is cooled to −78° C., 2 (8.63 g, 49.25 mmol) is added and stirring continued at −78° C. for 1.5 h. Saturated sodium bicarbonate (100 mL) is added and the mixture is allowed to warm to rt. The mixture is extracted with EtOAc (4×100 mL) and the organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8) to provide 15 g (76%) of the title compound as a mixture of two diastereomers in an equimolecular ratio. M+H+=399.37.

Workup

  1. concentrationThe mixture is concentrated
  2. dissolutionthe residue dissolved in dichloromethane (200 mL)
  3. temperaturecooled to 0° C
  4. temperaturethe mixture is warmed to room temperature over 2 hours
  5. temperatureThe mixture is cooled to −78° C.
  6. stirringstirring
  7. waitcontinued at −78° C. for 1.5 h
  8. temperatureto warm to rt
  9. extractionThe mixture is extracted with EtOAc (4×100 mL)
  10. customdried
  11. concentrationconcentrated under vacuum
  12. customThe residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:8)

Sources & evidence

ORD record
ord-4b4676d8f0c54914b0b770a60ef616ca
Source dataset
uspto-grants-2008_09
Patent number
US07419975B2

Linked notes

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