Triethylamine → HCID 86669725, compound

HRID 45585Notes

Reaction equation

HRID 45585 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[C:12]([OH:14])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC(C)C)=O.C(N(CC)CC)C.C[Si]([CH:34]=[N+:35]=[N-:36])(C)C.O.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[N+:35](=[CH:34][C:12]([C@@H:9]1[CH2:10][CH2:11][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:14])=[N-:36]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 167693TrimethylsilyldiazomethaneHCID 2734495(2S)-1-((tert-butoxy)carbonyl)azetidine-2-carboxylic acidHCID 86585896Sodium bicarbonate water

Product 1

HCID 86669725HCID 86669725, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-1-(tert-butoxycarbonyl)azetidine-2-carboxylic acid (1.80 g, 8.95 mmol) in tetrahydrofuran (90.0 mL) was cooled to 0° C., and isobutyl chloroformate (1.30 mL, 9.85 mmol) and triethylamine (1.50 mL, 10.7 mmol) were added. After stirring for 1 hour at room temperature, ammonium salt was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in acetonitrile (90.0 mL), and trimethylsilyldiazomethane (13.5 mL, 26.8 mmol) was added. After stirring for 7 hours at room temperature, to the mixture were added saturated sodium bicarbonate water and ethyl acetate. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with water and brine, and then dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified with silica gel column (hexane/ethyl acetate=90/10 to 75/25) to give the title compound (1.40 g, 6.22 mmol, 69%).

Workup

  1. filtrationammonium salt was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe obtained residue was dissolved in acetonitrile (90.0 mL)
  4. stirringAfter stirring for 7 hours at room temperature, to the mixture
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washthe organic layer was washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified with silica gel column (hexane/ethyl acetate=90/10 to 75/25)

Sources & evidence

ORD record
ord-3e3eeacd92d04cb4b3352c5fa72006de
Source dataset
uspto-grants-2013_09
Patent number
US08541585B2

Reaction notes

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