CN110240551A - Fmoc-β-Ala-Gly-OH的制备方法 - Google Patents
Fmoc-β-Ala-Gly-OH的制备方法 Download PDFInfo
- Publication number
- CN110240551A CN110240551A CN201910554677.2A CN201910554677A CN110240551A CN 110240551 A CN110240551 A CN 110240551A CN 201910554677 A CN201910554677 A CN 201910554677A CN 110240551 A CN110240551 A CN 110240551A
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- China
- Prior art keywords
- fmoc
- ala
- gly
- acid solution
- preparation
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- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- 239000002904 solvent Substances 0.000 claims abstract description 24
- 229910052769 Ytterbium Inorganic materials 0.000 claims abstract description 21
- 150000002148 esters Chemical class 0.000 claims abstract description 21
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 59
- 239000007787 solid Substances 0.000 claims description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 239000011734 sodium Substances 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 14
- 238000001914 filtration Methods 0.000 claims description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- 230000020477 pH reduction Effects 0.000 claims description 10
- 238000000746 purification Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 238000004809 thin layer chromatography Methods 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 238000005360 mashing Methods 0.000 claims description 3
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims description 3
- 235000019796 monopotassium phosphate Nutrition 0.000 claims description 3
- 229910000403 monosodium phosphate Inorganic materials 0.000 claims description 3
- 235000019799 monosodium phosphate Nutrition 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 claims description 3
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 claims description 3
- 229910000343 potassium bisulfate Inorganic materials 0.000 claims description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 3
- 238000001514 detection method Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 238000007086 side reaction Methods 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 102000004196 processed proteins & peptides Human genes 0.000 abstract description 2
- 230000036632 reaction speed Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CGIHPACLZJDCBQ-UHFFFAOYSA-N acibenzolar Chemical compound SC(=O)C1=CC=CC2=C1SN=N2 CGIHPACLZJDCBQ-UHFFFAOYSA-N 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- POYCVXKFJFKSOH-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3-(9h-fluoren-9-ylmethoxycarbonylamino)propanoate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)NCCC(=O)ON1C(=O)CCC1=O POYCVXKFJFKSOH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- -1 Hydrogen furans Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000010532 solid phase synthesis reaction Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 2
- YKOQQFDCCBKROY-UHFFFAOYSA-N n,n-diethylpropanamide Chemical compound CCN(CC)C(=O)CC YKOQQFDCCBKROY-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- LINBWYYLPWJQHE-UHFFFAOYSA-N 3-(9h-fluoren-9-ylmethoxycarbonylamino)propanoic acid Chemical compound C1=CC=C2C(COC(=O)NCCC(=O)O)C3=CC=CC=C3C2=C1 LINBWYYLPWJQHE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- QDHYJVJAGQLHBA-UHFFFAOYSA-N beta-Ala-Gly Chemical compound NCCC(=O)NCC(O)=O QDHYJVJAGQLHBA-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- WUWHFEHKUQVYLF-UHFFFAOYSA-M sodium;2-aminoacetate Chemical compound [Na+].NCC([O-])=O WUWHFEHKUQVYLF-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
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CN201910554677.2A CN110240551B (zh) | 2019-06-25 | 2019-06-25 | Fmoc-β-Ala-Gly-OH的制备方法 |
Applications Claiming Priority (1)
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CN201910554677.2A CN110240551B (zh) | 2019-06-25 | 2019-06-25 | Fmoc-β-Ala-Gly-OH的制备方法 |
Publications (2)
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CN110240551A true CN110240551A (zh) | 2019-09-17 |
CN110240551B CN110240551B (zh) | 2022-02-11 |
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CN201910554677.2A Active CN110240551B (zh) | 2019-06-25 | 2019-06-25 | Fmoc-β-Ala-Gly-OH的制备方法 |
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011047192A2 (en) * | 2009-10-14 | 2011-04-21 | Dana-Farber Cancer Institute, Inc. | Protected amine labels and use in detecting analytes |
CN103665109A (zh) * | 2013-11-15 | 2014-03-26 | 陕西东大生化科技有限责任公司 | 成骨生长肽碳端五肽的合成方法 |
CN104059223A (zh) * | 2014-05-30 | 2014-09-24 | 浙江大学 | 稀土催化剂催化的聚类肽的合成方法及合成的聚类肽 |
CN105218644A (zh) * | 2015-11-09 | 2016-01-06 | 叶仲林 | 一种比伐卢定的制备方法 |
CN105451743A (zh) * | 2013-08-07 | 2016-03-30 | 箭头研究公司 | 用于在活体中递送RNAi触发子至肿瘤细胞的聚偶联物 |
-
2019
- 2019-06-25 CN CN201910554677.2A patent/CN110240551B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011047192A2 (en) * | 2009-10-14 | 2011-04-21 | Dana-Farber Cancer Institute, Inc. | Protected amine labels and use in detecting analytes |
CN105451743A (zh) * | 2013-08-07 | 2016-03-30 | 箭头研究公司 | 用于在活体中递送RNAi触发子至肿瘤细胞的聚偶联物 |
CN103665109A (zh) * | 2013-11-15 | 2014-03-26 | 陕西东大生化科技有限责任公司 | 成骨生长肽碳端五肽的合成方法 |
CN104059223A (zh) * | 2014-05-30 | 2014-09-24 | 浙江大学 | 稀土催化剂催化的聚类肽的合成方法及合成的聚类肽 |
CN105218644A (zh) * | 2015-11-09 | 2016-01-06 | 叶仲林 | 一种比伐卢定的制备方法 |
Non-Patent Citations (1)
Title |
---|
RYO YOSHINO等: "Fmoc-OPhth, the reagent of Fmoc protection", 《TETRAHEDRON LETTERS》 * |
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Publication number | Publication date |
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CN110240551B (zh) | 2022-02-11 |
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PB01 | Publication | ||
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GR01 | Patent grant | ||
GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Fmoc- b- Preparation method of Ala-Gly-OH Effective date of registration: 20230105 Granted publication date: 20220211 Pledgee: Chengdu Rural Commercial Bank Co.,Ltd. Pujiang Xilai Guzhen Sub branch Pledgor: CHENGDU ZHENGYUAN BIOCHEMICAL TECHNOLOGY CO.,LTD. Registration number: Y2023510000001 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20231228 Granted publication date: 20220211 Pledgee: Chengdu Rural Commercial Bank Co.,Ltd. Pujiang Xilai Guzhen Sub branch Pledgor: CHENGDU ZHENGYUAN BIOCHEMICAL TECHNOLOGY CO.,LTD. Registration number: Y2023510000001 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Fmoc- b- Preparation method of Ala Gly OH Granted publication date: 20220211 Pledgee: Chengdu Rural Commercial Bank Co.,Ltd. Pujiang Xilai Guzhen Sub branch Pledgor: CHENGDU ZHENGYUAN BIOCHEMICAL TECHNOLOGY CO.,LTD. Registration number: Y2024510000001 |