Benzyl isocyanate → HCID 54483168, compound

HRID 1066021Notes

Reaction equation

HRID 1066021 reaction equation
[CH2:1]([C@@H:8]1[NH:11][C:10](=[O:12])[C@H:9]1[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:24]([N:31]=[C:32]=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1.CCOC(C)=O>[CH2:24]([NH:31][C:32]([N:11]1[C@@H:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:9]([CH3:13])[C:10]1=[O:12])=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 76639Benzyl isocyanateHCID 2733832Lithium HexamethyldisilazideHCID 10535250HCID 10535250, compound

Product 1

HCID 54483168HCID 54483168, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4(S)-benzyl-3(S)-methylazetidin-2-one (50 mg, 0.28 mmol) in THF (4 mL) at −78°, lithium bis(trimethylsilyl)amide (280 μL, 280 mmol, 1 M in THF) was added. After 10 min, benzyl isocyanate (37.2 mg, 34.6 μL, 0.28 mmol) was added. Stirring was continued at −78° for 45 min. The reaction mixture was diluted with EtOAc (50 mL) and washed with aqueous NaHSO4 (1M) and brine, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (SiO2, 14% EtOAc in hexane) to give the title compound 4(S)-benzyl-3(S)-methyl-2-oxoazetidine-1-carboxylic acid benzylamide (23 mg, 27% yield) as a colorless oil. 1H-NMR (400 MHz, CDCl3) δ7.38-7.19 (m, 10H), 6.94 (t, J=5.1 Hz, 1H), 4.53 (dd, J=14.9, 6.0 Hz, 1 H), 4.48 (dd, J=14.9, 6.0 Hz, 1H), 3.90 (ddd, J=8.6, 3.2, 2.9 Hz, 1H), 3.53 (dd, J=13.7, 3.5 Hz, 1 H), 2.95 (qd, J=7.6, 2.5 Hz, 1H), 2.92 (dd, J=13.3, 8.9 Hz, 1H), 1.14 (d, J=7.6 Hz, 3H); FAB MS m/z 309.3 (MH+); HRMS calcd for C19H21N2O2: 309.1603 (MH+); found: 309.1614.

Workup

  1. waitwas continued at −78° for 45 min
  2. washwashed with aqueous NaHSO4 (1M) and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (SiO2, 14% EtOAc in hexane)

Sources & evidence

ORD record
ord-a751bc90ec9840e9b597915db8f0bad7
Source dataset
uspto-grants-2001_06
Patent number
US06242439B1

Reaction notes

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