Intermediate for synthesizing prostaglandin drugs and its preparation method
A technology for prostaglandins and intermediates, which is applied in the field of intermediates for the synthesis of prostaglandins, and can solve the problems that prostaglandins cannot meet the needs of clinical medication and their content is low
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Embodiment 1
[0031] Embodiment 1: Preparation of compound Iaa
[0032]
[0033] Compound Iaa is synthesized as follows:
[0034]
[0035] step 1):
[0036] Under a nitrogen atmosphere, triethylamine (2.5 mL) was added to a solution of compound IV (1.0 g, purchased from Shanghai Julong Pharmaceutical Research and Development Co., Ltd.) in dichloromethane (50 mL). The reaction system was cooled to -78°C, and a solution of triisopropylsilyl triflate (2.9 g) in dichloromethane (10 mL) was added. After two hours, the cooling bath was removed, and the reaction system was stirred at 20°C for 30 minutes. The reaction system was concentrated under reduced pressure, and the residue was purified by column chromatography to obtain compound Vaa.
[0037] 1 HNMR (400MHz, CDCl 3 ): δ4.94-4.89(m, 1H), 4.18-4.11(m, 1H), 3.84(dd, J=9.6, 5.2Hz, 1H), 3.69(dd, J=10.4, 7.2Hz, 1H), 2.79(dd, J=18, 10.8Hz, 1H), 2.63-2.60(m, 1H), 2.53-2.45(m, 2H), 2.70(s, 1H), 2.05-1.97(m, 2H), 1.14- 1.01(m, 21H)
[0...
Embodiment 2
[0044] Embodiment 2: preparation compound Iab
[0045]
[0046] Using a method similar to the synthesis of compound Iaa, compound Iab was synthesized.
[0047] 1 H-NMR (400MHz, CDCl 3 ( m, 4H), 2.39~2.33(m, 1H), 2.19~2.00(m, 5H), 1.89~1.85(m, 3H), 1.73~1.58(m, 3H), 1.13~1.09(m, 3H), 0.89~0.85(m, 9H), 0.07~0.02(m, 6H)
Embodiment 3
[0048] Embodiment 3: preparation compound Iac
[0049]
[0050] Compound lac was synthesized using a method similar to the synthesis of compound Iaa.
[0051] 1 H-NMR (400MHz, CDCl 3 )δ5.98~5.96(m, 1H), 5.41~5.34(m, 2H), 4.14~4.10(m, 2H), 3.76~3.72(m, 1H), 3.49~3.45(m, 1H), 3.34~ 3.28(m, 2H), 3.22~3.17(m, 2H), 2.40~2.32(m, 1H), 2.18~2.10(m, 4H), 2.05~1.99(m, 1H), 1.85~1.83(br, 3H ), 1.71~1.58(m, 3H), 1.48~1.40(m, 2H), 1.35~1.28(m, 2H), 0.90~0.85(m, 3H), 0.84~0.83(m, 9H), 0.05~0.01 (m, 6H)
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