* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Sc., 1933, p. 1617
[2] Sc., 1933, p. 1617
[3] Helvetica Chimica Acta, 1952, vol. 35, p. 75,76,77
[4] Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 57, # 1/2, p. 37 - 49
[5] Journal of Organic Chemistry, 1995, vol. 60, # 15, p. 4767 - 4773
[6] Journal of Medicinal Chemistry, 1998, vol. 41, # 5, p. 682 - 690
[7] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 6, p. 533 - 535
[8] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 6, p. 533 - 535
[9] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 11, p. 1420 - 1432
[10] Organic letters, 2001, vol. 3, # 9, p. 1395 - 1397
[11] Patent: US2008/182842, 2008, A1, . Location in patent: Page/Page column 53
2
[ 1619-62-1 ]
[ 5471-77-2 ]
Yield
Reaction Conditions
Operation in experiment
80%
Stage #1: With potassium hydroxide In ethanol at 20℃; for 12 h; Stage #2: With hydrogenchloride In water
Potassium hydroxide (7.5 g, 131.5 mmol) is added to a solution of Compound 46 (25.0 g, 132.8 mmol) in 100.0 mL of ethanol. The solution is stirred at rom temperature for 12 h, the solvent is removed under reduced pressure. The obtained solid is dissolved in water and extracted with diethyl ether; the aqueous layer is acidified with 6N aqueous HCl solution to pH 4 and then extracted with ethyl acetate. The combined ethyl acetate layers are washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford 17.0 g of Compound 47 as an orange liquid. Yield: 80percent; m/z 161 [M+H].
58.8%
With potassium hydroxide In ethanol; water for 1 h; Reflux
Step 2. To a solution of compound 19-2 (3.0 g, 15.94 mmol) in EtOH (20 mL) was added aq. KOH solution (85percent, 894 mg, 15.94 mmol). The reaction mixture was heated at reflux for 1 h. After organic solvent was removed under reduced pressure, it was diluted with H20 (20 mL), and washed with PE (10 mL x 2). The aqueous phase was adjusted to pH 2 with cone. HC1 solution and extracted with EtOAc (20 mL x 3). The combined EtOAc layer was dried over Na2S04, filtered, and concentrated under reduced pressure to afford compound 19-3 (1.5 g, 58.8 percent). NMR (400 MHz, DMSO-/) δ 3.98 - 3.93 (q, 4H), 1.17 (s, 6H), 1.12 (t, J= 7.2 Hz, 3H).
Reference：
[1] Patent: WO2007/20936, 2007, A1, . Location in patent: Page/Page column 114-115
[2] Patent: US2011/71196, 2011, A1, . Location in patent: Page/Page column 31
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6790 - 6802
[4] Patent: WO2015/95227, 2015, A2, . Location in patent: Page/Page column 101; 102
[5] Helvetica Chimica Acta, 1935, vol. 18, p. 1279
[6] Journal of the Chemical Society, 1933, p. 1617
[7] Journal of the American Chemical Society, 1984, vol. 106, # 8, p. 2353 - 2358
[8] Patent: EP2036887, 2009, A1, . Location in patent: Page/Page column 60
[9] Patent: EP1548024, 2005, A1, . Location in patent: Page/Page column 72
[10] Molecules, 2016, vol. 21, # 5,
[11] Journal of Medicinal Chemistry, 2017, vol. 60, # 21, p. 9067 - 9089
3
[ 3495-36-1 ]
[ 97-63-2 ]
[ 5471-77-2 ]
Reference：
[1] Patent: JP2016/132634, 2016, A, . Location in patent: Paragraph 0064-0068
4
[ 801301-34-8 ]
[ 124-38-9 ]
[ 5471-77-2 ]
Reference：
[1] Chemistry - A European Journal, 2011, vol. 17, # 19, p. 5272 - 5280
5
[ 124-38-9 ]
[ 97-62-1 ]
[ 5471-77-2 ]
Reference：
[1] Tetrahedron Letters, 1971, p. 3001 - 3004
With C22H31F3GeO3P2PdS In N,N-dimethyl-formamide at 100℃; for 6h; Inert atmosphere;
4
Under a nitrogen atmosphere,Complex 4 (1.7 mg, 0.0025 mmol),Cesium formate (26.7 mg, 0.15 mmol),Ethyl methacrylate (11.4 mg, 0.1 mmol) N, N-dimethylformamide (2 mL) was added to a glass reaction vessel,And heated at 100 ° C. for 6 hours.After cooling, hydrochloric acid (2 N, 2 ml, 2 mmol) was added,Extraction was carried out by adding diethyl ether (4 ml, 38.5 mmol)After removal of solvent under reduced pressure,1 H-NMR was measured,From the ratio to the internal standard substance tetrachloroethane,It was confirmed that the product 5 was produced in a yield of 50 mol%.
Stage #1: 3-ethoxy-2,2-dimethyl-3-oxopropanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.166667h;
Stage #2: N-ethylbenzylamine In dichloromethane at 20℃; for 2h;
2.b
The product of a) (680 mg, 4.25 mmol) was dissolved in 10 mL dichloromethane. HOBT (859 mg, 6.38 mmol) and EDCI (1.22 g, 6.38 mmol) were added, and after stirring for 10 min, ethyl benzylamine (632 mg, 4.68 mmol) was added. After stirring at room temperature for 2 hours, the material disappeared by TLC. Concentrate, add 100mL of dichloromethane, wash once with 10% dilute hydrochloric acid, wash once, wash once with saturated brine, 15mL each time, concentrate the organic phase, petroleum ether: ethyl acetate = 8:1 column chromatography, to obtain colorless liquid 919 mg (yield: 78%).
The product of a) of Example 2(680 mg, 4.25 mmol) was dissolved in 10 mL dichloromethane.HOBT (859 mg, 6.38 mmol) and EDCI (1.22 g, 6.38 mmol) were added, and after stirring for 10 min, <strong>[51537-21-4]O-tert-butyl-L-serine tert-butyl ester hydrochloride</strong> (1.19 g, 4.68 mmol) was added. After stirring at room temperature for 2 hours, the material disappeared by TLC. Concentrate, add 100mL of dichloromethane, wash once with 10% dilute hydrochloric acid, wash once, wash once with saturated brine, 15mL each time, concentrate the organic phase, petroleum ether: ethyl acetate = 8:1 column chromatography, get white solid 1.05 g (yield: 69%).
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