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

HRID 355219노트

반응식

HRID 355219 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

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%.

후처리

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

출처 및 근거

ORD 기록
ord-276f9670cd5e44c0be4448ab3c6c7aa7
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04378314

반응 노트

불러오는 중…