CN109734627A - A kind of new compound N -2- alkanoyl-N-6- fluorenylmethyloxycarbonyl-L-lysine - Google Patents
A kind of new compound N -2- alkanoyl-N-6- fluorenylmethyloxycarbonyl-L-lysine Download PDFInfo
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- CN109734627A CN109734627A CN201910158689.3A CN201910158689A CN109734627A CN 109734627 A CN109734627 A CN 109734627A CN 201910158689 A CN201910158689 A CN 201910158689A CN 109734627 A CN109734627 A CN 109734627A
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Abstract
The present invention relates to the new compounds of a kind of N-2- alkanoyl-N-6- fluorenylmethyloxycarbonyl-L-lysine (hereinafter referred to as compound 1).The structural formula of compound 1:Wherein n=1~18, preferred (CH2)nIt is all straight chain；Fmoc is fluorenylmethyloxycarbonyl.N-2- alkanoyl-N-6- fluorenylmethyloxycarbonyl-L-lysine is applied to field of medicaments as a kind of derivative compound of new L-lysine.
Description
Technical field
The present invention relates to the new of a kind of N-2- alkanoyl-N-6- fluorenylmethyloxycarbonyl-L-lysine (hereinafter referred to as compound 1)
Type compound.
Technical background
The derivative of L-lysine uses available a series of peptide modified compound in Peptides Synthesis, this
Polypeptide compound after modification has many functions and purposes in field of medicaments.N-2- alkanoyl-N-6- fluorenes methoxy carbonyl of the present invention
A kind of derivative compound of the base-L-lysine as new L-lysine, is applied to field of medicaments.
Summary of the invention
The invention reside in synthesizing, N-2- alkanoyl-N-6- fluorenylmethyloxycarbonyl-L-lysine (compound 1) is a new class of
Compound.
The structural formula of compound 1:
Wherein n=1~18, preferred (CH2)nIt is all straight chain；Fmoc is fluorenylmethyloxycarbonyl.
The present invention also provides N-2- alkanoyl-N-6- fluorenylmethyloxycarbonyl-L-lysine preparation methods.
Preparation method includes the following steps:
1) using N-6- benzyl-L-lysine and alkane acyl chlorides or alkane acylbromide as raw material, with alkali in water or water-miscible organic solvent
Or both mixture in react, be made compound N -2- alkanoyl-N-6- benzyl-L-lysine；
2) compound N -2- alkanoyl-N-6- benzyl-L-lysine is raw material, in a solvent, de- with palladium carbon catalytic hydrogenation
The benzyl group on the amino on 6 N is gone, compound N -2- alkanoyl-L-lysine is obtained；
3) using compound N -2- alkanoyl-L-lysine and fluorenes methoxy dicarbonyl chloride as raw material, have with alkali in water or water solubility
It is reacted in the mixture of solvent or both, obtains the reaction solution of compound 1, reaction solution is concentrated, crystallization, and filtering is made.
Reaction equation is as follows:
Wherein, Fmoc is-fluorenylmethyloxycarbonyl,
HX is HCl or HBr；
N=1~18.
The present invention provides new compound N -2- alkanoyl-N-6- fluorenylmethyloxycarbonyl-L-lysine, new as one kind
The derivative compound of L-lysine is applied to field of medicaments.
Specific embodiment
Below in conjunction with specific embodiment, the present invention will be further explained.Raw material used in the present invention
It is bought from market.
Embodiment 1: the synthesis (20) of compound 1
Potassium carbonate 2.8g is sequentially added into reaction flask, water 9ml, tetrahydrofuran 9ml, N-6- tertbutyloxycarbonyl-L- rely ammonia
Eicosane acyl chlorides 1.60g is added dropwise in sour 1.0g, room temperature, is added dropwise and finishes, and reacts 1 hour, and reaction is finished, and 30~40 DEG C are removed under reduced pressure tetrahydro furan
It mutters, then with hydrochloric acid tune PH to 2.0, filters, dry cake obtains N-2- eicosane acyl group-N-6 tertbutyloxycarbonyl-L-lysine
1.9g, yield 86%, purity 98.7%.
N-2- eicosane acyl group-N-6 tertbutyloxycarbonyl-L-lysine 1.0g, trifluoroacetic acid 10ml is added into reaction flask,
Room temperature reaction 5 hours, reaction are finished, and 30~40 DEG C are removed under reduced pressure trifluoroacetic acid, then plus 10ml acetone, 1ml triethylamine filter, do
Dry filter cake obtains N-2- eicosane acyl group-L-lysine 0.75g, yield 88%, purity 98.7%
N-2- eicosane acyl group-L-lysine 0.5g, n,N dimethylformamide 9ml, carbonic acid are sequentially added into reaction flask
9- fluorenes methoxy dicarbonyl chloride 05g is added dropwise in hydrogen sodium 08g, room temperature, is added dropwise and finishes, and reacts 4 hours, and reaction is finished, and adds water 10ml, filters, dry
Filter cake obtains N-2- eicosane acyl group-N-6- fluorenylmethyloxycarbonyl-L-lysine 0.6g, yield 90%, purity 97%.ESI-MS:[M-
H]-m/z 661。
Embodiment 1: the synthesis (18) of compound 1
Potassium carbonate 2.8g is sequentially added into reaction flask, water 9ml, tetrahydrofuran 9ml, N-6- tertbutyloxycarbonyl-L- rely ammonia
Stearyl chloride 1.47g is added dropwise in sour 1.0g, room temperature, is added dropwise and finishes, and reacts 1 hour, and reaction is finished, and 30~40 DEG C are removed under reduced pressure tetrahydro furan
It mutters, then with hydrochloric acid tune PH to 2.0, filters, dry cake obtains N-2- octadecanoyl-N-6 tertbutyloxycarbonyl-L-lysine
1.9g, yield 86%, purity 98.7%.
N-2- octadecanoyl-N-6 tertbutyloxycarbonyl-L-lysine 1.0g, trifluoroacetic acid 10ml is added into reaction flask,
Room temperature reaction 5 hours, reaction are finished, and 30~40 DEG C are removed under reduced pressure trifluoroacetic acid, then plus 10ml acetone, 1ml triethylamine filter, do
Dry filter cake obtains N-2- octadecanoyl-L-lysine 0.75g, yield 88%, purity 98.7%
N-2- octadecanoyl-L-lysine 0.5g, n,N dimethylformamide 9ml, carbonic acid are sequentially added into reaction flask
9- fluorenes methoxy dicarbonyl chloride 07g is added dropwise in hydrogen sodium 0.51g, room temperature, is added dropwise and finishes, and reacts 4 hours, and reaction is finished, and adds water 10ml, filters, and does
Dry filter cake obtains N-2- octadecanoyl-N-6- fluorenylmethyloxycarbonyl-L-lysine 0.6g, yield 90%, purity 97%.ESI-MS:
[M-H]-m/z 633。
Embodiment 2: the synthesis (16) of compound 1
Potassium carbonate 2.8g is sequentially added into reaction flask, water 9ml, tetrahydrofuran 9ml, N-6- tertbutyloxycarbonyl-L- rely ammonia
Palmitoyl chloride 1g is added dropwise in sour 1.0g, room temperature, is added dropwise and finishes, and reacts 1 hour, and reaction is finished, and 30~40 DEG C are removed under reduced pressure tetrahydrofuran, then
It with hydrochloric acid tune PH to 2.0, filters, dry cake obtains N-2- palmityl-N-6 tertbutyloxycarbonyl-L-lysine 1.8g, yield
87.8%, purity 98.5%.
N-2- palmityl-N-6 tertbutyloxycarbonyl-L-lysine 1.0g, trifluoroacetic acid 10ml, room are added into reaction flask
Temperature reaction 5 hours, reaction is finished, and 30~40 DEG C are removed under reduced pressure trifluoroacetic acid, then plus 10ml acetone, 1ml triethylamine filter, it is dry
Filter cake obtains N-2- palmityl-L-lysine 0.78g, yield 97.5%, purity 98.7%
N-2- palmityl-L-lysine 0.5g, n,N dimethylformamide 9ml, bicarbonate are sequentially added into reaction flask
9- fluorenes methoxy dicarbonyl chloride 0.4g is added dropwise in sodium 0.54g, room temperature, is added dropwise and finishes, and reacts 4 hours, and reaction is finished, and adds water 10ml, filters, dry
Filter cake obtains N-2- palmityl-N-6- fluorenylmethyloxycarbonyl-L-lysine 0.74g, yield 80%, purity 98.7%.ESI-MS:
[M-H]-m/z 605。
Embodiment 3: the synthesis (14) of compound 1
Potassium carbonate 2.7g is sequentially added into reaction flask, water 9ml, tetrahydrofuran 9ml, N-6- tertbutyloxycarbonyl-L- rely ammonia
Myristyl chloride 1.2g is added dropwise in sour 1.0g (4.06mmol), room temperature, is added dropwise and finishes, and reacts 1 hour, and reaction is finished, 30~40 DEG C of decompressions
Tetrahydrofuran is removed, then with hydrochloric acid tune PH to 2.0, filtered, dry cake obtains N-2- tetradecane acyl group-N-6 tertbutyloxycarbonyl-L-
Lysine 1.7g, yield 86%, purity 98.7%.
N-2- tetradecane acyl group-N-6 tertbutyloxycarbonyl-L-lysine 1.0g, trifluoroacetic acid 10ml is added into reaction flask,
Room temperature reaction 5 hours, reaction are finished, and 30~40 DEG C are removed under reduced pressure trifluoroacetic acid, then plus 10ml acetone, 1ml triethylamine filter, do
Dry filter cake obtains N-2- tetradecane acyl group-L-lysine 0.70g, yield 88.5%, purity 98.7%
N-2- tetradecane acyl group-L-lysine 0.5g, n,N dimethylformamide 9ml, carbonic acid are sequentially added into reaction flask
9- fluorenes methoxy dicarbonyl chloride 0.44g is added dropwise in hydrogen sodium 0.59g, room temperature, is added dropwise and finishes, and reacts 4 hours, and reaction is finished, and adds water 10ml, filters,
Dry cake obtains N-2- tetradecane acyl group-N-6- fluorenylmethyloxycarbonyl-L-lysine 0.7g, yield 88%, purity 97%.ESI-
MS:[M-H]-m/z 577。
Embodiment 4: the synthesis (12) of compound 1
Potassium carbonate 2.7g is sequentially added into reaction flask, water 9ml, tetrahydrofuran 9ml, N-6- tertbutyloxycarbonyl-L- rely ammonia
Dodecane acyl chlorides 1.05g is added dropwise in sour 1.0g (4.06mmol), room temperature, is added dropwise and finishes, and reacts 1 hour, and reaction is finished, 30~40 DEG C of decompressions
Tetrahydrofuran is removed, then with hydrochloric acid tune PH to 2.0, filtered, dry cake obtains N-2- dodecane acyl group-N-6 tertbutyloxycarbonyl-L-
Lysine 1.6g, yield 86%, purity 98.7%.
N-2- dodecane acyl group-N-6 tertbutyloxycarbonyl-L-lysine 1.0g, trifluoroacetic acid 10ml is added into reaction flask,
Room temperature reaction 5 hours, reaction are finished, and 30~40 DEG C are removed under reduced pressure trifluoroacetic acid, then plus 10ml acetone, 1ml triethylamine filter, do
Dry filter cake obtains N-2- dodecane acyl group-L-lysine 0.72g, yield 92%, purity 98.7%
N-2- dodecane acyl group-L-lysine 0.5g, n,N dimethylformamide 9ml, carbonic acid are sequentially added into reaction flask
9- fluorenes methoxy dicarbonyl chloride 0.47g is added dropwise in hydrogen sodium 0.64g, room temperature, is added dropwise and finishes, and reacts 4 hours, and reaction is finished, and adds water 10ml, filters,
Dry cake obtains N-2- dodecane acyl group-N-6- fluorenylmethyloxycarbonyl-L-lysine 0.7g, yield 88%, purity 97%.ESI-
MS:[M-H]-m/z 549。
Embodiment 5: the synthesis (10) of compound 1
Potassium carbonate 2.7g is sequentially added into reaction flask, water 9ml, tetrahydrofuran 9ml, N-6- tertbutyloxycarbonyl-L- rely ammonia
Ten alkane acyl chlorides 0.95g are added dropwise in sour 1.0g (4.06mmol), room temperature, are added dropwise and finish, and react 1 hour, and reaction is finished, and 30~40 DEG C of decompressions remove
It removes tetrahydrofuran, then with hydrochloric acid tune PH to 2.0, filters, dry cake obtains ten alkanoyl-N-6 tertbutyloxycarbonyl-L- of N-2- and relies ammonia
Sour 1.6g, yield 86%, purity 98.7%.
Ten alkanoyl-N-6 tertbutyloxycarbonyl of N-2--L-lysine 1.0g, trifluoroacetic acid 10ml, room are added into reaction flask
Temperature reaction 5 hours, reaction is finished, and 30~40 DEG C are removed under reduced pressure trifluoroacetic acid, then plus 10ml acetone, 1ml triethylamine filter, it is dry
Filter cake obtains ten alkanoyls of N-2--L-lysine 0.72g, yield 92%, purity 98.7%
Ten alkanoyls of N-2--L-lysine 0.5g, n,N dimethylformamide 9ml, bicarbonate are sequentially added into reaction flask
9- fluorenes methoxy dicarbonyl chloride 0.52g is added dropwise in sodium 0.7g, room temperature, is added dropwise and finishes, and reacts 4 hours, and reaction is finished, and adds water 10ml, filters, dry
Filter cake obtains ten alkanoyl-N-6- fluorenylmethyloxycarbonyl of N-2--L-lysine 0.78g, yield 90%, purity 97%.ESI-MS:[M-
H]-m/z 521。
Embodiment 6: the synthesis (8) of compound 1
Potassium carbonate 2.7g is sequentially added into reaction flask, water 9ml, tetrahydrofuran 9ml, N-6- tertbutyloxycarbonyl-L- rely ammonia
Caprylyl chloride 0.80g is added dropwise in sour 1.0g (4.06mmol), room temperature, is added dropwise and finishes, and reacts 1 hour, and reaction is finished, and 30~40 DEG C are removed under reduced pressure
Tetrahydrofuran, then with hydrochloric acid tune PH to 2.0, filter, dry cake obtains N-2- caprylyl-N-6 tertbutyloxycarbonyl-L-lysine
1.4g, yield 92%, purity 98.7%.
N-2- caprylyl-N-6 tertbutyloxycarbonyl-L-lysine 1.0g, trifluoroacetic acid 10ml, room temperature are added into reaction flask
Reaction 5 hours, reaction are finished, and 30~40 DEG C are removed under reduced pressure trifluoroacetic acid, then plus 10ml acetone, 1ml triethylamine filter, dry filter
Cake obtains N-2- caprylyl-L-lysine 0.65g, yield 89%, purity 98.7%
N-2- caprylyl-L-lysine 0.5g, n,N dimethylformamide 9ml, sodium bicarbonate are sequentially added into reaction flask
9- fluorenes methoxy dicarbonyl chloride 0.57g is added dropwise in 0.77g, room temperature, is added dropwise and finishes, and reacts 4 hours, and reaction is finished, and adds water 10ml, filters, dry
Filter cake obtains N-2- caprylyl-N-6- fluorenylmethyloxycarbonyl-L-lysine 0.8g, yield 88%, purity 97%.ESI-MS:[M-H]-
m/z 493。
Embodiment 7: the synthesis (6) of compound 1
Potassium carbonate 2.7g is sequentially added into reaction flask, water 9ml, tetrahydrofuran 9ml, N-6- tertbutyloxycarbonyl-L- rely ammonia
Caproyl chloride 0.65g is added dropwise in sour 1.0g (4.06mmol), room temperature, is added dropwise and finishes, and reacts 1 hour, and reaction is finished, and 30~40 DEG C are removed under reduced pressure
Tetrahydrofuran, then with hydrochloric acid tune PH to 2.0, filter, dry cake obtains N-2- caproyl-N-6 tertbutyloxycarbonyl-L-lysine
1.25g, yield 89%, purity 98.7%.
N-2- caproyl-N-6 tertbutyloxycarbonyl-L-lysine 1.0g, trifluoroacetic acid 10ml, room temperature are added into reaction flask
Reaction 5 hours, reaction are finished, and 30~40 DEG C are removed under reduced pressure trifluoroacetic acid, then plus 10ml acetone, 1ml triethylamine filter, dry filter
Cake obtains N-2- caproyl-L-lysine 0.65g, yield 93%, purity 98.7%
N-2- caproyl-L-lysine 0.5g, n,N dimethylformamide 9ml, sodium bicarbonate are sequentially added into reaction flask
9- fluorenes methoxy dicarbonyl chloride 0.63g is added dropwise in 0.85g, room temperature, is added dropwise and finishes, and reacts 4 hours, and reaction is finished, and adds water 10ml, filters, dry
Filter cake obtains N-2- caproyl-N-6- fluorenylmethyloxycarbonyl-L-lysine 0.85g, yield 89%, purity 97%.ESI-MS:[M-H]-
m/z 465。
Embodiment 8: the synthesis (4) of compound 1
Potassium carbonate 2.7g is sequentially added into reaction flask, water 9ml, tetrahydrofuran 9ml, N-6- tertbutyloxycarbonyl-L- rely ammonia
Butyl chloride 0.51g is added dropwise in sour 1.0g (4.06mmol), room temperature, is added dropwise and finishes, and reacts 1 hour, and reaction is finished, and 30~40 DEG C are removed under reduced pressure
Tetrahydrofuran, then with hydrochloric acid tune PH to 2.0, filter, dry cake obtains N-2- bytyry-N-6 tertbutyloxycarbonyl-L-lysine
1.1g, yield 86%, purity 98.7%.
N-2- bytyry-N-6 tertbutyloxycarbonyl-L-lysine 1.0g, trifluoroacetic acid 10ml, room temperature are added into reaction flask
Reaction 5 hours, reaction are finished, and 30~40 DEG C are removed under reduced pressure trifluoroacetic acid, then plus 10ml acetone, 1ml triethylamine filter, dry filter
Cake obtains N-2- bytyry-L-lysine 0.63g, yield 93%, purity 98.7%
N-2- bytyry-L-lysine 0.5g, n,N dimethylformamide 9ml, sodium bicarbonate are sequentially added into reaction flask
9- fluorenes methoxy dicarbonyl chloride 0.71g is added dropwise in 0.97g, room temperature, is added dropwise and finishes, and reacts 4 hours, and reaction is finished, and adds water 10ml, filters, dry
Filter cake obtains N-2- bytyry-N-6- fluorenylmethyloxycarbonyl-L-lysine 0.88g, yield 88%, purity 97%.ESI-MS:[M-H]-
m/z 437。
Embodiment 8: the synthesis (3) of compound 1
Potassium carbonate 2.7g is sequentially added into reaction flask, water 9ml, tetrahydrofuran 9ml, N-6- tertbutyloxycarbonyl-L- rely ammonia
Propionyl chloride 0.44g is added dropwise in sour 1.0g (4.06mmol), room temperature, is added dropwise and finishes, and reacts 1 hour, and reaction is finished, and 30~40 DEG C are removed under reduced pressure
Tetrahydrofuran, then with hydrochloric acid tune PH to 2.0, filter, dry cake obtains the tertiary propylene carbonyl oxygen-L-lysine of N-2- propiono-N-6
1.0g, yield 80%, purity 98%.
N-2- propiono-N-6 tertbutyloxycarbonyl-L-lysine 1.0g, trifluoroacetic acid 10ml, room temperature are added into reaction flask
Reaction 5 hours, reaction are finished, and 30~40 DEG C are removed under reduced pressure trifluoroacetic acid, then plus 10ml acetone, 1ml triethylamine filter, dry filter
Cake obtains N-2- propiono-L-lysine 0.60g, yield 88%, purity 98.7%
N-2- propiono-L-lysine 0.5g, tetrahydrofuran 9ml, water 10m, sodium bicarbonate are sequentially added into reaction flask
9- fluorenes methoxy dicarbonyl chloride 0.77g is added dropwise in 0.83g, room temperature, is added dropwise and finishes, and reacts 4 hours, and reaction is finished, and tetrahydrofuran is recovered under reduced pressure, adds
Water 10ml, filters, and dry cake obtains N-2- propiono-N-6- fluorenylmethyloxycarbonyl-L-lysine 0.87g, yield 88%, purity
97%.ESI-MS:[M-H]-m/z 423。
Claims (3)
1. the following compound N -2- alkanoyl-N-6- fluorenylmethyloxycarbonyl-L-lysine of general formula
Wherein n=1~18；Fmoc is fluorenylmethyloxycarbonyl.
2. compound according to claim 1, it is characterised in that: (CH2)nIt is all straight chain.
3. compound according to claim 1, it is characterised in that: the preparation method of the compound includes the following steps:
1) using N-6- benzyl-L-lysine and alkane acyl chlorides or alkane acylbromide as raw material, with alkali in water or water-miscible organic solvent or two
It is reacted in the mixture of person, compound N -2- alkanoyl-N-6- benzyl-L-lysine is made；
2) compound N -2- alkanoyl-N-6- benzyl-L-lysine is that raw material sloughs 6 in a solvent with palladium carbon catalytic hydrogenation
The benzyl group on amino on N obtains compound N -2- alkanoyl-L-lysine；
3) organic molten in water or water solubility with alkali using compound N -2- alkanoyl-L-lysine and fluorenes methoxy dicarbonyl chloride as raw material
It is reacted in the mixture of agent or both, obtains the reaction solution of compound 1, reaction solution is concentrated, crystallization, and filtering is made.
Reaction equation is as follows:
Wherein, Fmoc is-fluorenylmethyloxycarbonyl, and HX is HCl or HBr；N=1~18.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105121421A (en) * | 2012-11-05 | 2015-12-02 | 辉瑞公司 | Spliceostatin analogs |
| WO2017160669A1 (en) * | 2016-03-18 | 2017-09-21 | Merck Sharp & Dohme Corp. | Insulin-incretin conjugates |
| WO2017189342A1 (en) * | 2016-04-26 | 2017-11-02 | Merck Sharp & Dohme Corp. | Insulin dimer-incretin conjugates |
| WO2018181428A1 (en) * | 2017-03-29 | 2018-10-04 | 塩野義製薬株式会社 | Complex of nucleic acid medicine and multibranched lipid |
-
2019
- 2019-03-04 CN CN201910158689.3A patent/CN109734627A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105121421A (en) * | 2012-11-05 | 2015-12-02 | 辉瑞公司 | Spliceostatin analogs |
| WO2017160669A1 (en) * | 2016-03-18 | 2017-09-21 | Merck Sharp & Dohme Corp. | Insulin-incretin conjugates |
| WO2017189342A1 (en) * | 2016-04-26 | 2017-11-02 | Merck Sharp & Dohme Corp. | Insulin dimer-incretin conjugates |
| WO2018181428A1 (en) * | 2017-03-29 | 2018-10-04 | 塩野義製薬株式会社 | Complex of nucleic acid medicine and multibranched lipid |
Non-Patent Citations (6)
| Title |
|---|
| 刘美艳等: "N~α-9-芴甲氧羰基-N~ε-叔丁氧基羰基-L-赖氨酸的合成研究 ", 《精细化工中间体》 * |
| 姜和等: "Fmoc法肽合成中正交保护赖氨酸的研究进展 ", 《重庆理工大学学报(自然科学)》 * |
| 王丹等: "正交保护赖氨酸的制备 ", 《中国医药工业杂志》 * |
| 石常青等: "两种N-保护赖氨酸的合成 ", 《苏州大学学报(自然科学版)》 * |
| 石金桃等: "《有机合成化学》", 31 August 2017, 合肥工业大学出版社 * |
| 魏浩等: "保护赖氨酸的制备工艺 ", 《南京工业大学学报(自然科学版)》 * |
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