CN113461519A - Preparation method of octadecanedioic acid mono-tert-butyl ester-PFP - Google Patents
Preparation method of octadecanedioic acid mono-tert-butyl ester-PFP Download PDFInfo
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- CN113461519A CN113461519A CN202110923363.2A CN202110923363A CN113461519A CN 113461519 A CN113461519 A CN 113461519A CN 202110923363 A CN202110923363 A CN 202110923363A CN 113461519 A CN113461519 A CN 113461519A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/02—Preparation of carboxylic acid esters by interreacting ester groups, i.e. transesterification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Abstract
The invention discloses a preparation method of octadecanedioic acid mono-tert-butyl ester-PFP, which comprises the preparation of a compound 1 and the preparation of octadecanedioic acid mono-tert-butyl ester-PFP; the preparation of octadecanedioic acid mono-tert-butyl ester-PFP comprises the following steps: a1, adding the compound 1, pyridine and DMF (dimethyl formamide) into a reaction kettle, starting stirring, completely dissolving, dropwise adding trifluoroacetic acid pentafluorophenol ester, separating out a solid, and reacting again; a2, post-treatment: suction-filtering reaction liquid, collecting yellowish or white solid, pulping and suction-filtering DMF, collecting a product, and vacuum-drying to obtain 1.4Kg, wherein the prepared compound 1 has simple reaction and post-treatment, and can also be directly used for preparing octadecanedioic acid mono-tert-butyl ester-PFP, the solid generated by the reaction for preparing the octadecanedioic acid mono-tert-butyl ester-PFP is the product, the product with high purity can be obtained only by simple pulping, the coupling difficulty of the octadecanedioic acid or the octadecanedioic acid tert-butyl ester used for preparing the side chains of the polypeptides such as the Somalutide and the like is higher, the octadecanedioic acid mono-tert-butyl ester-PFP can react only by adding alkali, and the reaction efficiency is high.
Description
Technical Field
The invention relates to the technical field of medicine preparation, in particular to a preparation method of octadecanedioic acid mono-tert-butyl ester-PFP.
Background
Octadecanedioic acid is an important chemical raw material, belongs to one of long-chain dibasic acids, has very wide application, and can be used as a raw material to synthesize special nylon, high-grade spices, high-grade hot melt adhesives, cold-resistant plasticizers, high-grade lubricating oil, high-grade antirust agents, high-grade paints, coatings and the like;
however, in the current market, the coupling difficulty of octadecanedioic acid or tert-butyl ester of octadecanedioic acid used for preparing polypeptide side chains such as the somaglutide is high, the purity is low, and the method cannot be suitable for popularization and production.
Disclosure of Invention
The invention provides a preparation method of octadecanedioic acid mono-tert-butyl ester-PFP, which can effectively solve the problems that the coupling difficulty of octadecanedioic acid or tert-butyl ester of octadecanedioic acid used for preparing polypeptide side chains such as Somalutide and the like in the current market is high, the purity is low, and the method cannot be suitable for popularization and production.
In order to achieve the purpose, the invention provides the following technical scheme: a preparation method of octadecanedioic acid mono-tert-butyl ester-PFP, which comprises the preparation of a compound 1 and the preparation of octadecanedioic acid mono-tert-butyl ester-PFP;
wherein the preparation of the compound 1 comprises the following steps:
s1, adding octadecanedioic acid, toluene and tert-butyl alcohol into the reaction kettle, stirring, heating, and adding (Boc)2Stirring at room temperature overnight after the O reaction;
s2, post-processing: carrying out reduced pressure rotary evaporation on 10L of reaction liquid to 5L, adding a DCM solution to dilute to 10L, washing with 10L of water, filtering, separating and leaving an organic layer, washing with 10L of 5% phosphoric acid aqueous solution, separating and leaving the organic layer, and finally washing with 10L of saturated saline solution, separating and leaving the organic layer;
s3, carrying out reduced pressure rotary steaming on the organic layer until no liquid drops, cooling and solidifying, dissolving with ACN in a water bath, naturally cooling, crystallizing, solidifying, adding ACN for pulping, carrying out suction filtration by using a Buchner funnel, and collecting a product;
the preparation of octadecanedioic acid mono-tert-butyl ester-PFP comprises the following steps:
a1, adding the compound 1, pyridine and DMF (dimethyl formamide) into a reaction kettle, starting stirring, completely dissolving, dropwise adding trifluoroacetic acid pentafluorophenol ester, separating out a solid, and reacting again;
a2, post-treatment: and (3) carrying out suction filtration on the reaction solution, collecting yellowish or white solid, pulping and carrying out suction filtration on DMF (dimethyl formamide), collecting a product, and carrying out vacuum drying to obtain 1.4 Kg.
According to the technical scheme, the reaction kettle of S1 in the compound 1 is 50L, the heating temperature is 70 ℃, and the reaction time is 4.5 h.
According to the technical scheme, the ACN of S3 in the compound 1 is dissolved in a water bath at 60 ℃.
According to the technical scheme, the reaction kettle of the octadecanedioic acid mono-tert-butyl ester-PFP is 50L, 2Kg of compound 1, 1.5L of pyridine, 16L of DMF16L and 2.3L of pentafluorophenol trifluoroacetate are added, and the reaction time is 2.5-3 h.
According to the technical scheme, the compound 1 is prepared from octadecanedioic acid, tertiary butanol and (Boc) under the action of an organic solvent and a catalyst2O reaction is generated;
the organic solvent is any one or a mixture of several of dichloromethane, THF, toluene and DMF in any proportion;
the catalyst is 4-Dimethylaminopyridine (DMAP), the reaction temperature is 55-80 ℃, the reaction time is 4.5-24h, and a reaction product is subjected to post-treatment to obtain a compound 1;
the molar ratio of octadecanedioic acid, tertiary butanol, DMAP and Boc 2O is 1:8-10:0.1-0.5: 1.0-1.5.
According to the technical scheme, the octadecanedioic acid mono-tert-butyl ester-PFP has the esterification reaction of the compound 1 and pentafluorophenyl trifluoroacetate under the action of an organic solvent and an organic base;
the organic solution is one or a mixture of more of THF, dichloromethane, DMF, ethanol, methanol and toluene in any proportion;
the organic base is N-methylmorpholine (NMM), N-Diisopropylethylamine (DIEA) and pyridine;
the mass ratio of the compound 1 to the pyridine and the pentafluorophenyl trifluoroacetate is (1:0.5-1.5: 1.5-2.5).
Compared with the prior art, the invention has the beneficial effects that: the prepared compound 1 is simple in reaction and post-treatment, and can also be directly used for preparing octadecanedioic acid mono-tert-butyl ester-PFP, the solid generated in the reaction for preparing the octadecanedioic acid mono-tert-butyl ester-PFP is a product, a high-purity product can be obtained only by simple pulping, the coupling difficulty of octadecanedioic acid or octadecanedioic acid tert-butyl ester used for preparing polypeptide side chains such as Somalutide is high, the octadecanedioic acid mono-tert-butyl ester-PFP can be reacted only by adding alkali, and the reaction efficiency is high.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the principles of the invention and not to limit the invention.
In the drawings:
FIG. 1 is a chart of the end of reaction HPLC of mono-tert-butyl octadecanedioate-PFP according to the invention.
Detailed Description
The preferred embodiments of the present invention will be described in conjunction with the accompanying drawings, and it will be understood that they are described herein for the purpose of illustration and explanation and not limitation.
Example 1:
as shown in figure 1, the invention provides a technical scheme, a preparation method of octadecanedioic acid mono-tert-butyl ester-PFP,
comprises the preparation of compound 1 and the preparation of octadecanedioic acid mono-tert-butyl ester-PFP;
wherein the preparation of the compound 1 comprises the following steps:
s1, adding octadecanedioic acid, toluene and tert-butyl alcohol into the reaction kettle, stirring, heating, and adding (Boc)2Stirring at room temperature overnight after the O reaction;
the reaction kettle of S1 in the compound 1 is 50L, the heating temperature is 70 ℃, and the reaction time is 4.5 h;
s2, post-processing: carrying out reduced pressure rotary evaporation on 10L of reaction liquid to 5L, adding a DCM solution to dilute to 10L, washing with 10L of water, filtering, separating and leaving an organic layer, washing with 10L of 5% phosphoric acid aqueous solution, separating and leaving the organic layer, and finally washing with 10L of saturated saline solution, separating and leaving the organic layer;
s3, carrying out reduced pressure rotary steaming on the organic layer until no liquid drops, cooling and solidifying, dissolving with ACN in a water bath, naturally cooling, crystallizing, solidifying, adding ACN for pulping, carrying out suction filtration by using a Buchner funnel, and collecting a product;
the ACN of S3 in compound 1 was dissolved in a water bath at 60 ℃.
The preparation of octadecanedioic acid mono-tert-butyl ester-PFP comprises the following steps:
a1, adding the compound 1, pyridine and DMF (dimethyl formamide) into a reaction kettle, starting stirring, completely dissolving, dropwise adding trifluoroacetic acid pentafluorophenol ester, separating out a solid, and reacting again;
a2, post-treatment: and (3) carrying out suction filtration on the reaction solution, collecting yellowish or white solid, pulping and carrying out suction filtration on DMF (dimethyl formamide), collecting a product, and carrying out vacuum drying to obtain 1.4 Kg.
According to the technical scheme, the reaction kettle of octadecanedioic acid mono-tert-butyl ester-PFP is 50L, 2Kg of compound 1, 1.5L of pyridine, 16L of DMF16L and 2.3L of pentafluorophenol trifluoroacetate are added, and the reaction time is 2.8 h.
According to the technical scheme, the compound 1 is generated by reacting octadecanedioic acid with tert-butyl alcohol and (Boc)2O under the action of an organic solvent and a catalyst;
and the organic solvent is toluene;
wherein the catalyst is 4-Dimethylaminopyridine (DMAP), the reaction temperature is 65 ℃, the reaction time is 8 hours, and the reaction product is subjected to post-treatment to obtain a compound 1;
the molar ratio of octadecanedioic acid to tert-butanol to DMAP (Boc)2O was 1:9:0.3: 1.2.
According to the technical scheme, the octadecanedioic acid mono-tert-butyl ester-PFP has the esterification reaction of the compound 1 and pentafluorophenyl trifluoroacetate (perfluorophenyl 2,2,2-trifluoroacetate) under the action of an organic solvent and an organic base;
the organic solution is DMF;
the organic base is pyridine;
the mass ratio of the compound 1 to pyridine and pentafluorophenyl trifluoroacetate is (1:0.8: 2.2).
Example 2:
as shown in figure 1, the invention provides a technical scheme, a preparation method of octadecanedioic acid mono-tert-butyl ester-PFP,
comprises the preparation of compound 1 and the preparation of octadecanedioic acid mono-tert-butyl ester-PFP;
wherein the preparation of the compound 1 comprises the following steps:
s1, adding octadecanedioic acid, toluene and tert-butyl alcohol into the reaction kettle, stirring, heating, and adding (Boc)2Stirring at room temperature overnight after the O reaction;
s2, post-processing: carrying out reduced pressure rotary evaporation on 10L of reaction liquid to 5L, adding a DCM solution to dilute to 10L, washing with 10L of water, filtering, separating and leaving an organic layer, washing with 10L of 5% phosphoric acid aqueous solution, separating and leaving the organic layer, and finally washing with 10L of saturated saline solution, separating and leaving the organic layer;
s3, carrying out reduced pressure rotary steaming on the organic layer until no liquid drops, cooling and solidifying, dissolving with ACN in a water bath, naturally cooling, crystallizing, solidifying, adding ACN for pulping, carrying out suction filtration by using a Buchner funnel, and collecting a product;
the preparation of octadecanedioic acid mono-tert-butyl ester-PFP comprises the following steps:
a1, adding the compound 1, pyridine and DMF (dimethyl formamide) into a reaction kettle, starting stirring, completely dissolving, dropwise adding trifluoroacetic acid pentafluorophenol ester, separating out a solid, and reacting again;
a2, post-treatment: and (3) carrying out suction filtration on the reaction solution, collecting yellowish or white solid, pulping and carrying out suction filtration on DMF (dimethyl formamide), collecting a product, and carrying out vacuum drying to obtain 1.4 Kg.
According to the technical scheme, the reaction kettle of S1 in the compound 1 is 50L, the heating temperature is 70 ℃, and the reaction time is 4.5 h.
According to the technical scheme, the ACN of S3 in the compound 1 is dissolved in a water bath at 60 ℃.
According to the technical scheme, the reaction kettle of octadecanedioic acid mono-tert-butyl ester-PFP is 50L, 2Kg of compound 1, 1.5L of pyridine, 16L of DMF16L and 2.3L of pentafluorophenol trifluoroacetate are added, and the reaction time is 2.5 h.
According to the technical scheme, the compound 1 is prepared from octadecanedioic acid, tertiary butanol and (Boc) under the action of an organic solvent and a catalyst2O reaction is generated;
the organic solvent is dichloromethane;
the catalyst is 4-Dimethylaminopyridine (DMAP), the reaction temperature is 70 ℃, the reaction time is 5.5 hours, and the reaction product is subjected to post-treatment to obtain a compound 1;
the molar ratio of octadecanedioic acid to tert-butanol to DMAP (Boc)2O was 1:9:0.3: 1.3.
According to the technical scheme, the octadecanedioic acid mono-tert-butyl ester-PFP is prepared by carrying out esterification reaction on the compound 1 and perfluorophenyl trifluoroacetate (perfluorophenyl 2,2,2-trifluoroacetate) in the presence of an organic solvent and an organic base;
the organic solution is THF;
the organic base is N-methylmorpholine (NMM);
the mass ratio of the compound 1 to pyridine and pentafluorophenyl trifluoroacetate is (1:0.9: 1.8).
Compared with the prior art, the invention has the beneficial effects that: the prepared compound 1 is simple in reaction and post-treatment, and can also be directly used for preparing octadecanedioic acid mono-tert-butyl ester-PFP, the solid generated in the reaction for preparing the octadecanedioic acid mono-tert-butyl ester-PFP is a product, a high-purity product can be obtained only by simple pulping, the coupling difficulty of octadecanedioic acid or octadecanedioic acid tert-butyl ester used for preparing polypeptide side chains such as Somalutide is high, the octadecanedioic acid mono-tert-butyl ester-PFP can be reacted only by adding alkali, and the reaction efficiency is high.
Finally, it should be noted that: although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that changes may be made in the embodiments and/or equivalents thereof without departing from the spirit and scope of the invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (6)
1. A preparation method of octadecanedioic acid mono-tert-butyl ester-PFP is characterized by comprising the following steps: comprises the preparation of compound 1 and the preparation of octadecanedioic acid mono-tert-butyl ester-PFP;
wherein the preparation of the compound 1 comprises the following steps:
s1, adding octadecanedioic acid, toluene and tert-butyl alcohol into the reaction kettle, stirring, heating, and adding (Boc)2Stirring at room temperature overnight after the O reaction;
s2, post-processing: carrying out reduced pressure rotary evaporation on 10L of reaction liquid to 5L, adding a DCM solution to dilute to 10L, washing with 10L of water, filtering, separating and leaving an organic layer, washing with 10L of 5% phosphoric acid aqueous solution, separating and leaving the organic layer, and finally washing with 10L of saturated saline solution, separating and leaving the organic layer;
s3, carrying out reduced pressure rotary steaming on the organic layer until no liquid drops, cooling and solidifying, dissolving with ACN in a water bath, naturally cooling, crystallizing, solidifying, adding ACN for pulping, carrying out suction filtration by using a Buchner funnel, and collecting a product;
the preparation of octadecanedioic acid mono-tert-butyl ester-PFP comprises the following steps:
a1, adding the compound 1, pyridine and DMF (dimethyl formamide) into a reaction kettle, starting stirring, completely dissolving, dropwise adding trifluoroacetic acid pentafluorophenol ester, separating out a solid, and reacting again;
a2, post-treatment: and (3) carrying out suction filtration on the reaction solution, collecting yellowish or white solid, pulping and carrying out suction filtration on DMF (dimethyl formamide), collecting a product, and carrying out vacuum drying to obtain 1.4 Kg.
2. The preparation method of octadecanedioic acid mono-tert-butyl ester-PFP according to claim 1, wherein the reaction kettle of S1 in the compound 1 is 50L, the heating temperature is 70 ℃, and the reaction time is 4.5 h.
3. The method for preparing octadecanedioic acid mono-tert-butyl ester-PFP according to claim 1, wherein the ACN of S3 in the compound 1 is dissolved in a water bath at 60 ℃.
4. The preparation method of octadecanedioic acid mono-tert-butyl ester-PFP according to claim 1, wherein the reaction kettle is 50L, 2Kg of compound 1, 1.5L of pyridine, 16L of DMF, and 2.3L of pentafluorophenol trifluoroacetate are added, and the reaction time is 2.5-3 h.
5. The preparation method of octadecanedioic acid mono-tert-butyl ester-PFP according to claim 1, wherein compound 1 is prepared by reacting octadecanedioic acid with tert-butanol, (Boc)2O under the action of organic solvent and catalyst;
the organic solvent is any one or a mixture of several of dichloromethane, THF, toluene and DMF in any proportion;
the catalyst is 4-Dimethylaminopyridine (DMAP), the reaction temperature is 55-80 ℃, the reaction time is 4.5-24h, and a reaction product is subjected to post-treatment to obtain a compound 1;
octadecanedioic acid tert-butanol DMAP (Boc)2The molar ratio of O is 1:8-10:0.1-0.5: 1.0-1.5.
6. The preparation method of octadecanedioic acid mono-tert-butyl ester-PFP according to claim 1, wherein the octadecanedioic acid mono-tert-butyl ester-PFP comprises the esterification of the compound 1 with pentafluorophenyl trifluoroacetate in the presence of an organic solvent and an organic base;
the organic solution is one or a mixture of more of THF, dichloromethane, DMF, ethanol, methanol and toluene in any proportion;
the organic base is N-methylmorpholine (NMM), N-Diisopropylethylamine (DIEA) and pyridine;
the mass ratio of the compound 1 to the pyridine and the pentafluorophenyl trifluoroacetate is (1:0.5-1.5: 1.5-2.5).
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113759048A (en) * | 2021-10-14 | 2021-12-07 | 成都普赛唯新生物科技有限公司 | Inspection method of mono-tert-butyl octadecanedioate |
| CN115368234A (en) * | 2022-08-19 | 2022-11-22 | 淄博矿业集团有限责任公司 | Synthesis method of important intermediate of Somaloutide side chain |
| CN115650852A (en) * | 2022-12-28 | 2023-01-31 | 天津卡普希科技有限公司 | Preparation method of octadecanedioic acid mono-tert-butyl ester |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104519902A (en) * | 2012-05-08 | 2015-04-15 | 诺和诺德A/S（股份有限公司） | Double-acylated GLP-1 derivatives |
| CN107108698A (en) * | 2014-11-14 | 2017-08-29 | 百时美施贵宝公司 | Macrocyclic peptides as immunomodulator |
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2021
- 2021-08-12 CN CN202110923363.2A patent/CN113461519A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104519902A (en) * | 2012-05-08 | 2015-04-15 | 诺和诺德A/S（股份有限公司） | Double-acylated GLP-1 derivatives |
| CN107108698A (en) * | 2014-11-14 | 2017-08-29 | 百时美施贵宝公司 | Macrocyclic peptides as immunomodulator |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113759048A (en) * | 2021-10-14 | 2021-12-07 | 成都普赛唯新生物科技有限公司 | Inspection method of mono-tert-butyl octadecanedioate |
| CN113759048B (en) * | 2021-10-14 | 2022-06-21 | 成都普康唯新生物科技有限公司 | Inspection method of mono-tert-butyl octadecanedioate |
| CN115368234A (en) * | 2022-08-19 | 2022-11-22 | 淄博矿业集团有限责任公司 | Synthesis method of important intermediate of Somaloutide side chain |
| CN115368234B (en) * | 2022-08-19 | 2024-01-26 | 淄博矿业集团有限责任公司 | Synthetic method of cable Ma Lutai side chain and intermediate thereof |
| CN115650852A (en) * | 2022-12-28 | 2023-01-31 | 天津卡普希科技有限公司 | Preparation method of octadecanedioic acid mono-tert-butyl ester |
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