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

HRID 893928노트

반응식

HRID 893928 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-4645c8697b3a40b9ba5f0068bf2d3055
출처 데이터셋
uspto-grants-1981_08
특허 번호
US04282150

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