A kind of preparation method of n-boc biphenylalaninaldehyde
A technology of biphenylalaninaldehyde and biphenylalaninol, which is applied in the field of medicine and chemical industry, can solve the problems of cumbersome operation and low yield, and achieve the effects of simple operation, high yield and high purity
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Embodiment 1
[0030] Example 1 (R)-N-Boc-3-(1,1'-biphenyl-4-yl)-2-aminopropanal
[0031] In a 1L round bottom flask, dissolve 105g of (R)-N-Boc-3-(1,1'-biphenyl-4-yl)-2-aminopropanol in 600mL of DME, and add 117g IBX. After the addition, the reaction system was heated to 75-85°C, and the reaction was monitored for about 1 hour until the raw materials disappeared, and the reaction system was cooled down to room temperature. Filtrate, rinse the filter cake with 50mL DME, collect the filter cake as 2-iodosobenzoic acid for subsequent recovery, concentrate the filtrate under reduced pressure, crystallize with ethyl acetate / n-heptane, and dry to obtain white 101 g of solid is the target product. The yield is 96.6%, and the purity is >99%.
[0032] 1 H-NMR (400MHz, CDCl 3 ):δ=9.69(s,1H),7.59(t,4H),7.46(t,2H),7.38(t,1H),7.28(d,2H),5.13(d,1H),4.48(q, 1H), 3.18(d, 2H), 1.47(s, 9H).
Embodiment 2
[0033] Embodiment 2 prepares IBX with the 2-iodosoylbenzoic acid that reclaims
[0034] In a 1L round-bottomed flask, add the 2-iodosobenzoic acid recovered in 40g of the above-mentioned Example 1, add a good aqueous solution of potassium persulfate (145g of potassium persulfate is dissolved in 500mL of water, the amount of potassium persulfate Active ingredient content is 42.8%). After the addition, the reaction system was heated up to 65-75° C., and reacted for about 3 hours. It was monitored that the residual 2-iodosobenzoic acid was less than 2%. The reaction system was cooled down to 0-5°C and stirred for 2 hours. After filtering, the filter cake was washed with water several times, and after drying, 38.6 g of white solid was obtained, which was IBX. The recovery rate was 85.4%, and the purity was >98%.
Embodiment 3
[0035] Example 3 (R)-N-Boc-3-(1,1'-biphenyl-4-yl)-2-aminopropionaldehyde (IBX is prepared from recovered 2-iodosobenzoic acid)
[0036] In a 250mL round bottom flask, dissolve 26g of (R)-N-Boc-3-(1,1'-biphenyl-4-yl)-2-aminopropanol in 160mL of DME, and add 29g of the IBX prepared in Example 2 were recovered. After the addition, the reaction system was heated to 75-85°C, and the reaction was monitored for about 1 hour until the raw materials disappeared, and the reaction system was cooled down to room temperature. After filtration, the filter cake was rinsed with 15 mL of DME, and the filter cake was collected as 2-iodosobenzoic acid, which could be reused for subsequent recovery. After the filtrate was concentrated under reduced pressure, it was crystallized with ethyl acetate / n-heptane, and after drying, 25 g of white solid was obtained, which was the target product. Yield 96.4%, purity>99%.
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