Triethylamine → 1-t-Butyldimethylsilyl-4-tritylthio-2-azetidinone

HRID 1758488Notes

Reaction equation

HRID 1758488 reaction equation
C(N(CC)CC)C.[C:8]([S:27][CH:28]1[NH:31][C:30](=[O:32])[CH2:29]1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl[Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35]>CN(C=O)C.O.CCOCC>[Si:34]([N:31]1[CH:28]([S:27][C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:29][C:30]1=[O:32])([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 127801644-Tritylthio-2-azetidinone

Product 1

HCID 129287451-t-Butyldimethylsilyl-4-tritylthio-2-azetidinoneYield 93.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Triethylamine (1.62 ml, 11.6 mmoles) was added dropwise in 5 min to a cooled (0°) and stirred solution of 4-tritylthio-2-azetidinone (3.5 g, 10.1 mmoles) and chloro-t-butyldimethylsilane (1.68 g, 12.7 mmoles) in DMF (35 ml). The reaction mixture was stirred at room temperature for 18 h, diluted with water (250 ml) and ether (200 ml). The organic phase was washed with water (3×50 ml), dried and concentrated to leave an oil (4.33 g). Crystallization from pentane gave a total of 4.1 g(89%) of the title compound as a white solid, m.p. 113°-4°. δ (ppm, CDCl3): 7.45 (15H, m, aromatics), 4.2 (1H, dd, H-4), 2.63 (1H, dd, J=4, J=16, H-3), 2.13 (1H, dd, J=2, J=16, H-3), 1.0 (9H, s, t-Bu), 0.35 (6H, s, Me). νc=o 1735 cm-1. Anal. calc'd for C28H33NOSSi: C, 73.15; H, 7.24; N, 3.05; S, 6.97%. Found: C, 73.27; H, 7.32; N, 2.97; S 6.94%.

Workup

  1. temperaturea cooled (0°)
  2. washThe organic phase was washed with water (3×50 ml)
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-98a16cda18184f67b1513b9e0708421d
Source dataset
uspto-grants-1983_02
Patent number
US04374065

Reaction notes

Loading…