JP6984054B2 - カンナビノイドの製造方法 - Google Patents
カンナビノイドの製造方法 Download PDFInfo
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- JP6984054B2 JP6984054B2 JP2021019616A JP2021019616A JP6984054B2 JP 6984054 B2 JP6984054 B2 JP 6984054B2 JP 2021019616 A JP2021019616 A JP 2021019616A JP 2021019616 A JP2021019616 A JP 2021019616A JP 6984054 B2 JP6984054 B2 JP 6984054B2
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- chloride
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- 0 CC(C)=CCCC(C)=CCc(c(O)c(C(OC)=O)c(CCCC*)c1)c1O Chemical compound CC(C)=CCCC(C)=CCc(c(O)c(C(OC)=O)c(CCCC*)c1)c1O 0.000 description 1
- GSBCCWIIKCFQKI-ZWKOTPCHSA-N CCCCCc1cc(O)c([C@@H]2C=C(C)CC[C@H]2C(C)=C)c(O)c1C(OC)=O Chemical compound CCCCCc1cc(O)c([C@@H]2C=C(C)CC[C@H]2C(C)=C)c(O)c1C(OC)=O GSBCCWIIKCFQKI-ZWKOTPCHSA-N 0.000 description 1
- UNMUUDYIISWCLT-DLBZAZTESA-N CCCCCc1cc([O]=C(C)[C@H]2[C@H]3C=C(C)CC2)c3c(O)c1 Chemical compound CCCCCc1cc([O]=C(C)[C@H]2[C@H]3C=C(C)CC2)c3c(O)c1 UNMUUDYIISWCLT-DLBZAZTESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
で表される化合物の加水分解脱炭酸を含む、以下の式(I):
で表されるカンナビジオールの製造方法を提供する。
Claims (15)
- 除去される前記溶媒は、30℃より高く100℃より低い沸点を有するC5〜C7炭化水素である、請求項1に記載の方法。
- 前記溶媒は、ヘキサンである、請求項2に記載の方法。
- 前記加熱は、101℃〜130℃の範囲で行われる、請求項1に記載の方法。
- 前記の塩基は、3〜5の当量を有する、請求項1に記載の方法。
- 前記の塩基は、アルカリ金属の水酸化物である、請求項1に記載の方法。
- 前記の塩基は、KOHまたはNaOHである、請求項6に記載の方法。
- 前記のルイス酸は、三フッ化ホウ素エーテラート、塩化アルミニウム、塩化インジウム、トリメチルシリルトリフルオロメタンスルホネート、塩化第二スズ、塩化亜鉛、トリフルオロメタンスルホン酸亜鉛、塩化第二鉄、塩化第一鉄、塩化チタン、スカンジウムトリメチルシリルトリフルオロメタンスルホネート、およびランタントリフルオロメタンスルホネートからなる群から選択される、請求項8に記載の方法。
- 前記のルイス酸は、三フッ化ホウ素エーテラートである、請求項9に記載の方法。
- 前記のブレンステッド酸は、p-トルエンスルホン酸またはトリフルオロ酢酸である、請求項8に記載の方法。
- 前記の式(III)で表される化合物において、R1がHであり、R2がC5アルキル基であり、R3がC1-C2アルキル基であり、AがHである、請求項8に記載の方法。
- 前記の式(I)で表される化合物において、R1がHであり、R2がC5アルキル基であり、AがHである、請求項1に記載の方法。
- 前記の式(II)で表される化合物において、R1がHであり、R2がC5アルキル基であり、R3がC1-C2アルキル基であり、AがHである、請求項1に記載の方法。
- 前記の保護基は、トリ−i−プロピルシリルオキシメチル(TOM)、(フェニルジメチルシリル)メトキシメチル(SMOM)、アセチル(Ac)、ピバロイル(Piv)、ベンゾアート(Bz)、トリメチルシリル(TMS)、t−ブチルジメチルシリル(TBDMS)、トリイソプロピルシリル(TIPS)、トリ(トリメチルシリル)シリル(TTMSS)、およびt−ブチルジフェニルシリル(TBDPS)からなる群から選択される、請求項1に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US16/795,851 US10981849B1 (en) | 2020-02-20 | 2020-02-20 | Method for preparing cannabinoids |
US16/795,851 | 2020-02-20 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2021130654A JP2021130654A (ja) | 2021-09-09 |
JP6984054B2 true JP6984054B2 (ja) | 2021-12-17 |
Family
ID=75495084
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2021019616A Active JP6984054B2 (ja) | 2020-02-20 | 2021-02-10 | カンナビノイドの製造方法 |
Country Status (4)
Country | Link |
---|---|
US (1) | US10981849B1 (ja) |
JP (1) | JP6984054B2 (ja) |
CA (1) | CA3093271C (ja) |
TW (1) | TWI738586B (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20220317097A1 (en) * | 2021-04-05 | 2022-10-06 | Grant Kraus | Atmospheric Triphasic Chromatography (ATC) method |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA200802767B (en) * | 2005-09-29 | 2009-09-30 | Amr Technology Inc | Process for production of delta-9-tetrahydrocannabinol |
US20170008869A1 (en) * | 2015-07-10 | 2017-01-12 | Noramco, Inc. | Process for the production of cannabidiol and delta-9-tetrahydrocannabinol |
EP3723752A4 (en) * | 2017-12-11 | 2021-10-20 | Artelo Biosciences, Inc. | NEW SOLID FORMS OF CANNABIDIOL AND USES OF IT |
CN111039761B (zh) * | 2019-12-31 | 2021-01-15 | 江苏汉邦科技有限公司 | 大麻二酚的纯化方法 |
-
2020
- 2020-02-20 US US16/795,851 patent/US10981849B1/en active Active
- 2020-09-16 CA CA3093271A patent/CA3093271C/en active Active
- 2020-12-11 TW TW109143882A patent/TWI738586B/zh active
-
2021
- 2021-02-10 JP JP2021019616A patent/JP6984054B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
TWI738586B (zh) | 2021-09-01 |
JP2021130654A (ja) | 2021-09-09 |
TW202132246A (zh) | 2021-09-01 |
US10981849B1 (en) | 2021-04-20 |
CA3093271C (en) | 2021-11-30 |
CA3093271A1 (en) | 2021-08-20 |
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