CN105087684A - Preparation method of tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate - Google Patents
Preparation method of tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate Download PDFInfo
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Abstract
The invention discloses a preparation method of tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate, wherein the preparation method comprises the following steps: adding proper amount of pure water to a reaction kettle as a solvent, and adding hydrophosphate to prepare a pH buffer solution which is 0.05mol/L-0.15mol/L in molar concentration; reacting at 45-55 DEG C for 10-15h by taking (S)-tert-butyl-6-benzyloxy-5-hydroxy-3-oxohexanoate as a reaction substrate, and during the process, adding a sodium hydroxide buffer solution to keep the pH value of the entire reaction system at 5.5-7.0; and after reaction, sequentially filtering, extracting, decompressing and concentration, and rectifying so as to obtain a finished tert-butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate product, wherein carbonyl reductase serves as a biological catalyst and glucose is used as a hydrogen donor; the mass-volume concentration of the (S)-tert-butyl-6-benzyloxy-5-hydroxy-3-oxohexanoate is 8g/mL-17g/mL; and the dosage of the carbonyl reductase is 4-6% of (S)-tert-butyl-6-benzyloxy-5-hydroxy-3-oxohexanoate. The preparation method disclosed by the invention not only can reduce production cost and bring about benefits for energy conservation and emission reduction, but also can improve molar concentration.
Description
Technical field
The present invention relates to a kind of compounds process for production thereof, particularly the preparation method of chloro-3, the 5-dihydroxyl hecanoic acid t-butyl esters of a kind of (3R, 5S)-6-.
Background technology
At present, produce chloro-3, the 5-dihydroxyl hecanoic acid t-butyl esters of (3R, 5S)-6-by following chemical synthesis: adopt (the 3R that the chloro-5-hydroxyl of POTASSIUM BOROHYDRIDE catalytic reduction (S)-6--3-carbonyl hecanoic acid t-butyl ester obtains, 5S)-6-chloro-3,5-dihydroxyl hecanoic acid t-butyl ester, (3R, 5S)-6-chloro-3 that this method obtains in reaction process, 5-dihydroxyl hecanoic acid t-butyl ester is racemization, need to carry out chiral separation to it, molar yield far below 50%, and needs to use expensive reagent; In addition, before improving when preparing (3R, 5S)-6-chloro-3,5-dihydroxyl hecanoic acid t-butyl ester (chiral reduction), need just there is good optical selective at-80 ~-100 DEG C, otherwise isomer impurities will up to more than 15%, low temperature like this, generally only have and adopt cooled with liquid nitrogen to realize, therefore the equipment Requirement of industrialization will be very high, and the input of these specific equipments will up to more than 3,000,000 yuan, and cost is very high, and a large amount of electric energy will be consumed preparing in liquid nitrogen process; In actual production process, chloro-3, the 5-dihydroxyl hecanoic acid t-butyl esters of (3R, 5S) per ton-6-need the liquid nitrogen consuming upper kilostere, and this will consume a large amount of power consumptions, is very unfavorable for energy-saving and emission-reduction.
Summary of the invention
The technical problem to be solved in the present invention is for the deficiencies in the prior art, a kind of (3R is proposed, 5S)-6-chloro-3, the preparation method of 5-dihydroxyl hecanoic acid t-butyl ester, the preparation method being somebody's turn to do chloro-3, the 5-dihydroxyl hecanoic acid t-butyl esters of (3R, 5S)-6-can not only reduce production cost, be beneficial to energy-saving and emission-reduction, and in production reaction process, molar yield is higher.
The technical problem to be solved in the present invention is achieved through the following technical solutions.The present invention is a kind of (3R, 5S)-6-chloro-3, the preparation method of 5-dihydroxyl hecanoic acid t-butyl ester, its feature is: make solvent with appropriate purified water in a kettle., add hydrophosphate and be configured to the pH damping fluid that volumetric molar concentration is 0.05mol/L-0.15mol/L, reaction substrate is made with the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester, make this substrate that asymmetric reduction reaction occur under the existence of biological catalyst and hydrogen donor and generate (3R, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester solution, reaction times is 10-15h, temperature of reaction is 45-55 DEG C, adding sodium hydrate buffer solution in reaction process makes the pH value of whole reaction system remain between 5.5-7.0, successively through filtering after reaction, extraction and concentrating under reduced pressure step, obtain (3R, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester crude product, then steam can obtain (3R through essence, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester finished product, wherein, described biological catalyst is carbonyl reductase, and described hydrogen donor is glucose, in reaction system when reacting initial, the mass volume ratio concentration of the described chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester is 8g/mL-17g/mL, and carbonyl reductase usage quantity is the 4%-6% of the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester.
One (3R of the present invention, 5S)-6-chloro-3, in the technical scheme of the preparation method of 5-dihydroxyl hecanoic acid t-butyl ester, preferred technical scheme feature is further: in reaction system when reacting initial, the mass volume ratio concentration of the substrate of the described chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester is 12g/mL.
One (3R of the present invention, 5S)-6-chloro-3, in the technical scheme of the preparation method of 5-dihydroxyl hecanoic acid t-butyl ester, preferred technical scheme feature is further: described carbonyl reductase usage quantity is 5% of the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester quality.
In the technical scheme of the preparation method of chloro-3, the 5-dihydroxyl hecanoic acid t-butyl esters of one (3R, 5S)-6-of the present invention, preferred technical scheme feature is further: the pH value of described whole reaction system remains between 6.4-6.6.
In the technical scheme of the preparation method of chloro-3, the 5-dihydroxyl hecanoic acid t-butyl esters of one (3R, 5S)-6-of the present invention, preferred technical scheme feature is further: the pH value of the whole reaction system stated remains on 6.5.
In the technical scheme of the preparation method of chloro-3, the 5-dihydroxyl hecanoic acid t-butyl esters of one (3R, 5S)-6-of the present invention, preferred technical scheme feature is further: the described reaction times is 12h, and temperature of reaction is 49 DEG C.
In the technical scheme of the preparation method of chloro-3, the 5-dihydroxyl hecanoic acid t-butyl esters of one (3R, 5S)-6-of the present invention, preferred technical scheme feature is further: described reactor is glassed steel reaction vessels.
In the technical scheme of the preparation method of chloro-3, the 5-dihydroxyl hecanoic acid t-butyl esters of one (3R, 5S)-6-of the present invention, preferred technical scheme feature is further: the volumetric molar concentration of described hydrophosphate is 0.05mol/L or 0.10mol/L.
Compared with prior art, the present invention has following technique effect:
Technique of the present invention is directly by the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester enzymatic clarification (3R, 5S)-6-chloro-3,5-dihydroxyl hecanoic acid t-butyl ester, the molar yield of preparation feedback reaches 80-88%, the content in crude product obtained is more than 96%, and be one-step synthesis, simplify reactions steps and operation steps, greatly save the time; And be react at normal temperatures, decrease equipment and artificial requirement, provide cost savings; And (S)-6-chloro-5-hydroxyl-3-carbonyl hecanoic acid t-butyl ester is cheap, provides cost savings further.
Embodiment
Below further describe concrete technical scheme of the present invention, so that those skilled in the art understands the present invention further, and do not form the restriction of its power.
Embodiment 1, a kind of (3R, 5S)-6-chloro-3, the preparation method of 5-dihydroxyl hecanoic acid t-butyl ester, comprise the steps: to make solvent with appropriate purified water in glassed steel reaction vessels, add hydrophosphate and be configured to the pH damping fluid that volumetric molar concentration is 0.05mol/L-0.15mol/L, reaction substrate is made with the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester, make this substrate that asymmetric reduction reaction occur under the existence of biological catalyst and hydrogen donor and generate (3R, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester solution, reaction times is 10-15h, temperature of reaction is 45-55 DEG C, adding sodium hydrate buffer solution in reaction process makes the pH value of whole reaction system remain between 5.5-7.0, successively through filtering after reaction, extraction and concentrating under reduced pressure step, obtain (3R, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester crude product, then steam can obtain (3R through essence, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester finished product, wherein, described biological catalyst is carbonyl reductase, and described hydrogen donor is glucose, in reaction system when reacting initial, the mass volume ratio concentration of the described chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester is 8g/mL-17g/mL, and carbonyl reductase usage quantity is the 4%-6% of the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester.
Embodiment 2, a kind of (3R, 5S)-6-chloro-3, the preparation method of 5-dihydroxyl hecanoic acid t-butyl ester, comprise the steps: to make solvent with purified water in glassed steel reaction vessels, be that the hydrophosphate solution of 0.10mol/L makes pH value of solution damping fluid with volumetric molar concentration, reaction substrate is made with the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester, make this substrate that asymmetric reduction reaction occur under the existence of biological catalyst and hydrogen donor and generate (3R, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester solution, reaction times is 12h, temperature of reaction is 50 DEG C, adding sodium hydrate buffer solution in reaction process makes the pH value of whole reaction system remain on 6.5, successively through filtering after reaction, extraction and concentrating under reduced pressure step, obtain (3R, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester crude product, then steam can obtain (3R through essence, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester finished product, wherein, described biological catalyst is carbonyl reductase, and described hydrogen donor is glucose, in reaction system when reacting initial, the mass volume ratio concentration of the described chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester is 12g/mL, and carbonyl reductase usage quantity is 5% of the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester.
Embodiment 3, a kind of (3R, 5S)-6-chloro-3, the preparation method of 5-dihydroxyl hecanoic acid t-butyl ester, comprise the steps: to make solvent with purified water in glassed steel reaction vessels, be that the hydrophosphate solution of 0.05mol/L makes pH value of solution damping fluid with volumetric molar concentration, reaction substrate is made with the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester, make this substrate that asymmetric reduction reaction occur under the existence of biological catalyst and hydrogen donor and generate (3R, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester solution, reaction times is 10h, temperature of reaction is 45 DEG C, adding sodium hydrate buffer solution in reaction process makes the pH value of whole reaction system remain on 5.5, successively through filtering after reaction, extraction and concentrating under reduced pressure step, obtain (3R, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester crude product, then steam can obtain (3R through essence, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester finished product, wherein, described biological catalyst is carbonyl reductase, and described hydrogen donor is glucose, in reaction system when reacting initial, the mass volume ratio concentration of the described chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester is 8g/mL, and carbonyl reductase usage quantity is 4% of the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester.
Embodiment 4, a kind of (3R, 5S)-6-chloro-3, the preparation method of 5-dihydroxyl hecanoic acid t-butyl ester, solvent is made with purified water in glassed steel reaction vessels, be that the hydrophosphate solution of 0.15mol/L makes pH value of solution damping fluid with volumetric molar concentration, reaction substrate is made with the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester, make this substrate that asymmetric reduction reaction occur under the existence of biological catalyst and hydrogen donor and generate (3R, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester solution, reaction times is 15h, temperature of reaction is 55 DEG C, adding sodium hydrate buffer solution in reaction process makes the pH value of whole reaction system remain on 7.0, successively through filtering after reaction, extraction and concentrating under reduced pressure step, obtain (3R, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester crude product, then steam can obtain (3R through essence, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester finished product, wherein, described biological catalyst is carbonyl reductase, and described hydrogen donor is glucose, in reaction system when reacting initial, the mass volume ratio concentration of the described chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester is 17g/mL, and carbonyl reductase usage quantity is 6% of the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester.
Embodiment 6, a kind of (3R, 5S)-6-chloro-3, the preparation method of 5-dihydroxyl hecanoic acid t-butyl ester, solvent is made with purified water in glassed steel reaction vessels, be that the hydrophosphate solution of 0.12mol/L makes pH value of solution damping fluid with volumetric molar concentration, reaction substrate is made with the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester, make this substrate that asymmetric reduction reaction occur under the existence of biological catalyst and hydrogen donor and generate (3R, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester solution, reaction times is 12h, temperature of reaction is 49 DEG C, adding sodium hydrate buffer solution in reaction process makes the pH value of whole reaction system remain on 6.5, successively through filtering after reaction, extraction and concentrating under reduced pressure step, obtain (3R, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester crude product, then steam can obtain (3R through essence, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester finished product, wherein, described biological catalyst is carbonyl reductase, and described hydrogen donor is glucose, in reaction system when reacting initial, the mass volume ratio concentration of the described chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester is 15g/mL, and carbonyl reductase usage quantity is 5.5% of the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester.
The phosphoric acid hydrogen used in all embodiments of the present invention is the mixture of salt Sodium phosphate dibasic and SODIUM PHOSPHATE, MONOBASIC, is pH buffer reagent conventional on market.
Technique of the present invention is directly by the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester enzymatic clarification (3R, 5S)-6-chloro-3,5-dihydroxyl hecanoic acid t-butyl ester, the molar yield of preparation feedback reaches 80-88%, the content in crude product obtained is more than 96%, and be one-step synthesis, simplify reactions steps and operation steps, greatly save the time; And be react at normal temperatures, decrease equipment and artificial requirement, provide cost savings; And (S)-6-chloro-5-hydroxyl-3-carbonyl hecanoic acid t-butyl ester is cheap, provides cost savings further.
Claims (8)
1. (a 3R, 5S)-6-chloro-3, the preparation method of 5-dihydroxyl hecanoic acid t-butyl ester, it is characterized in that, comprise the steps: to make solvent with appropriate purified water in a kettle., add hydrophosphate and be configured to the pH damping fluid that volumetric molar concentration is 0.05mol/L-0.15mol/L, reaction substrate is made with the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester, make this substrate that asymmetric reduction reaction occur under the existence of biological catalyst and hydrogen donor and generate (3R, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester solution, reaction times is 10-15h, temperature of reaction is 45-55 DEG C, adding sodium hydrate buffer solution in reaction process makes the pH value of whole reaction system remain between 5.5-7.0, successively through filtering after reaction, extraction and concentrating under reduced pressure step, obtain (3R, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester crude product, then steam can obtain (3R through essence, 5S)-6-chloro-3, 5-dihydroxyl hecanoic acid t-butyl ester finished product, wherein, described biological catalyst is carbonyl reductase, and described hydrogen donor is glucose, in reaction system when reacting initial, the mass volume ratio concentration of the described chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester is 8g/mL-17g/mL, and carbonyl reductase usage quantity is the 4%-6% of the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester.
2. (3R according to claim 1,5S)-6-chloro-3, the preparation method of 5-dihydroxyl hecanoic acid t-butyl ester, is characterized in that: in reaction system when reacting initial, and the mass volume ratio concentration of the substrate of the described chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester is 12g/mL.
3. the preparation method of chloro-3, the 5-dihydroxyl hecanoic acid t-butyl esters of (3R, 5S)-6-according to claim 1, is characterized in that: described carbonyl reductase usage quantity is 5% of the chloro-5-hydroxyl of (S)-6--3-carbonyl hecanoic acid t-butyl ester quality.
4. the preparation method of chloro-3, the 5-dihydroxyl hecanoic acid t-butyl esters of (3R, 5S)-6-according to claim 1, is characterized in that: the pH value of described whole reaction system remains between 6.4-6.6.
5. the preparation method of chloro-3, the 5-dihydroxyl hecanoic acid t-butyl esters of (3R, 5S)-6-according to claim 4, is characterized in that: the pH value of the whole reaction system stated remains on 6.5.
6. the preparation method of chloro-3, the 5-dihydroxyl hecanoic acid t-butyl esters of (3R, 5S)-6-according to claim 1, it is characterized in that: the described reaction times is 12h, temperature of reaction is 49 DEG C.
7. the preparation method of chloro-3, the 5-dihydroxyl hecanoic acid t-butyl esters of (3R, the 5S)-6-according to any one of claim 1-6, is characterized in that: described reactor is glassed steel reaction vessels.
8. the preparation method of chloro-3, the 5-dihydroxyl hecanoic acid t-butyl esters of (3R, the 5S)-6-according to any one of claim 1-6, is characterized in that: the volumetric molar concentration of described hydrophosphate is 0.05mol/L or 0.10mol/L.
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Application publication date: 20151125 |