Nitrogen → HCID 69904058, compound

HRID 2287526Notes

Reaction equation

HRID 2287526 reaction equation
[Si:1]([N:8]1[C@@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:10]([CH2:18][C:19]([CH2:21]O)=[CH2:20])[C:9]1=[O:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C(C)=CC=CC=1C.[Li+].[Cl-].CS([Cl:38])(=O)=O.N#N>CN(C=O)C.O>[Si:1]([N:8]1[C@@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:10]([CH2:18][C:19]([CH2:21][Cl:38])=[CH2:20])[C:9]1=[O:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 947NitrogenHCID 79372,6-LutidineHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 69904252HCID 69904252, compound

Product 1

HCID 69904058HCID 69904058, compoundYield 107%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred and ice-cooled slurry of (3S*,4R*)-1-tert-Butyldimethylsilyl-3-(2-hydroxymethyl-2-propenyl)-4-phenyl-2-azetidinone (13.66 g, 41.0 mmol), 2,6-lutidine (15.3 ml, d0.920, 123 mmol), and LiCl (anhydros, 4.37 g, 103 mmol) in DMF (103 ml) was added MeSO2Cl (MsCl, 7.93 ml, d1.480, 103 mmol) dropwise under an atmosphere of N2. After the reaction mixture was stirred with ice-cooling for 5 hours and 50 minutes, H2O (40 ml) was added. The stirring was continued at room temperature for additional 20 minutes to destroy the excess MsCl. The resultant dark red mixture was poured into H2O (70 ml). The mixture was extracted with Et2O (70 ml×5). The combined Et2O extracts were washed with H2O (×3), sat. NaHCO3 aq. solution (×1), and sat. NaCl aq. solution (×1), dried (MgSO4), treated with activated charcoal, and concentrated in vacuo to give practically pure title compound (15.36 g, quantitative) as a pale yellow oil. IRmax (film): 1735(v.s), 1650(w), 1175(s), 825(s), 750(s), 700(s) cm-1 ; 1H-NMR δ: 7.43-7.25(m, 5H), 5.14(br.s, 1H), 4.87(br.s, 1H), 4.22(d, J=2.6 Hz, 1H), 3.99(s, 2H), 3.25(ddd, J=10.1, 5.1, 2.6 Hz, 1H), 2.78(dd, J=16.1, 5.1 Hz, 1H), 2.60(dd, J=16.1, 10.1 Hz, 1H), 0.92(s, 9H), 0.22(s, 3H), -0.20(s, 3H) ppm. This was employed in the next step without further purification.

Workup

  1. stirringAfter the reaction mixture was stirred with ice-
  2. temperaturecooling for 5 hours and 50 minutes
  3. customto destroy the excess MsCl
  4. additionThe resultant dark red mixture was poured into H2O (70 ml)
  5. extractionThe mixture was extracted with Et2O (70 ml×5)
  6. washThe combined Et2O extracts were washed with H2O (×3), sat. NaHCO3 aq. solution (×1), and sat. NaCl aq. solution (×1)
  7. dry with materialdried (MgSO4)
  8. additiontreated with activated charcoal
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27a684d81f6b4695b31b558a02de3949
Source dataset
uspto-grants-2000_07
Patent number
US06083943

Reaction notes

Loading…