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

HRID 893928ノート

反応式

HRID 893928 の反応式
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]

参加物

7

反応物 3

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

生成物 1

HCID 129287451-t-Butyldimethylsilyl-4-tritylthio-2-azetidinone収率 93.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

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%.

後処理

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

出典と根拠

ORDレコード
ord-4645c8697b3a40b9ba5f0068bf2d3055
出典データセット
uspto-grants-1981_08
特許番号
US04282150

反応ノート

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