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A kind of net analogue intermediate and preparation method thereof
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A technology of analogs and intermediates, applied in the field of medicinal chemistry, can solve problems such as low yield and difficult purification
Inactive Publication Date: 2017-05-03
SHANGHAI INST OF TECH +1
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[0005] Aiming at the above-mentioned technical problems in the prior art, the present invention provides an intermediate of a net analog and a preparation method thereof, and the intermediate of a net analog and a preparation method thereof solve the problems of the prior art. The technical problems of low yield and difficult purification of pure drugs in the preparation process
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Embodiment 1
[0028] Example 1 Preparation of methyl 6-methyl-2-oxocyclohexyl-3-enecarboxylate
[0029]
[0030] Sodium wire (0.5g, 21.7mmol) was dropped into 150mL of absolute alcohol, after it was completely dissolved, 97.5 grams of methyl acetoacetate (97.5g, 840mmol) was added, cooled to 0°C, and then the E-crotonin Ethanol solution (52.5g, 749mmol of E-crotonin dissolved in 50mL of absolute ethanol), after the dropwise addition, stirred at room temperature overnight, the resulting yellow solution was cooled to 0°C, and then saturated with hydrogenchloride gas until hydrogen The spectrum shows that the hydrogen on the acetyl group at 2.0 disappears substantially, and the oily product 6-methyl-2-oxocyclohexyl-3-enecarboxylic acid methyl ester (75g, content 80%, Yield 48.7%). used directly in the next reaction.
[0033] The raw material 6-methyl-2-oxocyclohexyl-3-enecarboxylic acid methyl ester (2.8g, 16.6mmol) was placed in 10mL of acetic acid, and then bromine was added dropwise at 0°C (bromine 1.7mL, 33.1mmol dissolved in 15mL of acetic acid), after the dropwise addition was completed, the reaction was refluxed for 24 hours. Then it was poured into ice water, extracted with dichloromethane, washed with water, washed with saturated brine, dried over anhydroussodium sulfate, concentrated, and purified by column (R f = 0.75, PE: EA = 10: 1), to obtain khaki solid compound 3-bromo-6-methyl salicylate (0.3g, 1.2mmol, yield 7.4%). 1 HNMR (CDCl 3,300MHz)δ:11.98(s,1H),7.56(d,1H),6.66(d,1H),4.00(s,3H),2.59(s,3H).
Embodiment 3
[0034] Example 3 Preparation of 2-methoxy-3-bromo-6 methylbenzoate
[0035]
[0036] The raw material 3-bromo-6-methylsalicylic acid methyl ester (0.3g, 1.22mmol) was dissolved in 10mL of acetone, and iodomethane (0.6g, 3.61mmol) and potassiumcarbonate (0.4g, 2.90mmol) were added. Stir overnight at room temperature. Then filter, and wash the filter cake with acetone, concentrate the resulting mother liquor to dryness, and purify by column (Rf=0.70, PE:EA=10:1) to obtain oily 2-methoxy-3-bromo-6-methylbenzoic acid Methyl ester (0.3g, 1.16mmol, yield 95.1%). 1 HNMR (CDCl 3 ,300MHz)δ:7.47(d,1H),6.86(d,1H),3.94(s,3H),3.88(s,3H),2.28(s,3H).
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Abstract
The present invention provides a novel C-spiro-O-glycoside compound intermediate having a structural formula as shown in formula I. Also provided is a preparation method for the novel C-spiro-O-glycoside compound intermediate, comprising: first preparing 6-methyl-2-oxocyclohexyl-3-enecarboxylate; then preparing 3-bromo-6-methylsalicylic acid methyl ester; then preparing 2-methoxy-3-bromo-6-methylbenzoate; then preparing 2-methoxy-3-bromo-6-methylbenzoic acid; then preparing 3-bromo-methoxy-6-methyl-N, O-dimethyl hydroxybenzamide; then preparing (3-bromo-2-methoxy-6-methylphenyl)(4'-substituent benzyl)methanone; and then preparing (3-bromo-2-methoxy-6-methylphenyl)(4'-substituent benzyl)methane. The present invention avoids the formation of ortho / para isomers, and achieves a yield higher than 90%.
Description
technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a peptide compound, in particular to a peptide analog intermediate and a preparation method thereof. Background technique [0002] In recent years, sodiumglucose transporter 2 (sodium / glucose cotransporter 2, SGLT2) inhibitors have been hailed as a new hope for the treatment of diabetes. SGLT2 inhibitors mainly act on sodiumglucose transporter 2 in the proximal tubule of the kidney. The filtered glucose is reabsorbed in the kidney, and the glucose can pass through the nephron, Bellini tube and ureter, and finally be excreted in the urine, so as to remove excess glucose in the urine and achieve the purpose of controlling hyperglycemia (Minireviews inmedicinal chemistry (2010): 905-913.). Currently, SGLT2 inhibitors are marketed as canagliflozin, dapagliflozin and empagliflozin. [0003] [0004] These drugs are all modified on the basis of the structure of dapagliflozin, es...
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