CN103274936A - Chiral compound - Google Patents
Chiral compound Download PDFInfo
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- CN103274936A CN103274936A CN2013102437189A CN201310243718A CN103274936A CN 103274936 A CN103274936 A CN 103274936A CN 2013102437189 A CN2013102437189 A CN 2013102437189A CN 201310243718 A CN201310243718 A CN 201310243718A CN 103274936 A CN103274936 A CN 103274936A
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- Prior art keywords
- oac
- chipal compounds
- chiral compound
- synthesis
- carbonyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 17
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 6
- 238000010189 synthetic method Methods 0.000 claims abstract description 6
- 238000000926 separation method Methods 0.000 claims abstract description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 5
- QMXOFBXZEKTJIK-UHFFFAOYSA-N Glycinol Natural products C1=C(O)C=C2OCC3(O)C4=CC=C(O)C=C4OC3C2=C1 QMXOFBXZEKTJIK-UHFFFAOYSA-N 0.000 claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- JLXXLCJERIYMQG-UHFFFAOYSA-N phenylcyanamide Chemical compound N#CNC1=CC=CC=C1 JLXXLCJERIYMQG-UHFFFAOYSA-N 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- -1 compound 3-carbonyl-2(S)-phenyl-butyl acetate Chemical class 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000010992 reflux Methods 0.000 abstract description 2
- NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 abstract 2
- NJXPYZHXZZCTNI-UHFFFAOYSA-N 3-aminobenzonitrile Chemical compound NC1=CC=CC(C#N)=C1 NJXPYZHXZZCTNI-UHFFFAOYSA-N 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- FYMCOOOLDFPFPN-UHFFFAOYSA-K iron(3+);4-methylbenzenesulfonate Chemical compound [Fe+3].CC1=CC=C(S([O-])(=O)=O)C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 FYMCOOOLDFPFPN-UHFFFAOYSA-K 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000006561 solvent free reaction Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- ZNCGXYWZQVZPAI-UHFFFAOYSA-N triazanium tribromide Chemical compound [NH4+].[NH4+].[NH4+].[Br-].[Br-].[Br-] ZNCGXYWZQVZPAI-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a chiral compound which has the following chemical formula shown in the specification. A synthetic method of the chiral compound 3-carbonyl-2(S)-phenyl-butyl acetate comprises the steps of synthesis, separation and purification; reflux reaction of the 3-aminobenzonitrile for synthesis and chiral L-D-phenylglycinol is performed for 60 hours under the anhydrous and anaerobic conditions when Cu(OAc)2 H2O exits in chlorobenzene; and the use amount of Cu(OAc)2 H2O is 47.4 mol percent of the amount of the raw materials.
Description
One, technical field
The present invention relates to a kind of new compound and preparation method thereof, particularly a kind of chipal compounds and preparation method thereof exactly is preparation and the synthetic method thereof of a kind of chirality 3-carbonyl-2 (S)-phenyl-acetic acid butyl ester.
Two, background technology
3-carbonyl-2 (S)-phenyl-acetic acid butyl ester is important medicine intermediate, the existing lot of documents report of its synthetic method [1-2].
Reference:
1. Iron(III) tosylate catalyzed acylation of alcohols, phenols, and aldehydes，Baldwin, Neil J. et al Tetrahedron Letters, 53(51), 6946-6949;
2012.
2. N-Acyl 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) tetraphenylborate salts as O-acylating agents, Taylor, James E. et al, Tetrahedron Letters, 53(32), 4074-4076;
2012.
3. Triflic Acid Catalyzed Oxidative Lactonization and Diacetoxylation of Alkenes Using Peroxyacids as Oxidants, Kang, Yan-Biao and Gade, Lutz H., Journal of Organic Chemistry, 77(3), 1610-1615;
2012.
4. Investigation of the catalytic activity of an electron-deficient vanadium(IV) tetraphenylporphyrin: A new, highly efficient and reusable catalyst for ring-opening of epoxides ,Taghavi, S. Abdolmanaf et al, Polyhedron, 30(13), 2244-2252;
2011.
5. Mild Organic Ammonium Tribromide-Mediated Regioselective Ring Opening of Epoxides with Alcohols, Water, Acetic Anhydride, and Amines Under Solvent-Free Reaction Conditions, inghal, Sweety et al, Synthetic Communications, 41(12), 1829-1837;
2011.
6. Bis(NHC)-Palladium(II) Complex-Catalyzed Dioxygenation of Alkenes, Wang, Wenfeng et al ,Organometallics, 29(4), 928-933;
2010。
Three, summary of the invention
The present invention is intended to provide a kind of efficient chiral catalyst required chipal compounds part for the asymmetric synthesis field particularly prepares chiral drug, and technical problem to be solved is to select corresponding raw material and set up corresponding method synthesis of chiral catalyst ligand.
(1) the alleged chipal compounds of the present invention is the compound shown in the following chemical formula I:
（Ⅰ）。
Its chemical name: 3-carbonyl-2 (S)-phenyl-acetic acid butyl ester
The synthetic method of chipal compounds (I) is synthesized under catalyzer one hydrated copper acetate 47.4mol% existence condition in organic solvent with a cyano-aniline and chirality L-benzene glycinol respectively, and chemical equation is as follows:
That this chipal compounds (I) synthetic method comprises is synthetic, separation and purifying, described synthetic be exactly between cyano-aniline and chirality L-benzene glycinol Cu (OAc) is arranged in chlorobenzene
2H
2When O exists under the anhydrous and oxygen-free condition back flow reaction 60 hours, Cu (OAc)
2H
2The O consumption is the 47.4mol%(molar percentage of material quantity, down together).
The reaction mechanism of this reaction can be presumed as follows:
Between cyano-aniline under a large amount of Lewis acid one hydrated copper acetate effects, discharge two molecule acetic acid, with chirality (S)-benzene glycinol effect, intramolecular condensation is sloughed a part water and a part ammonia again, forms target compound I.
The preparation of this chipal compounds, adopt simple and easy, methodology of organic synthesis efficiently, the one-step synthesis chipal compounds, through the X-diffraction, NMR, its structure is determined in IR and ultimate analysis.
Four, description of drawings
Fig. 1 is the single crystal diffraction figure of compound (I).
Five, embodiment
1. the preparation of 3-carbonyl-2-phenyl-acetic acid butyl ester
In the 100mL two-mouth bottle, under the anhydrous and oxygen-free condition, add Cu(OAc)
2H
2O1.6g (8.04mmol), the 40ml chlorobenzene, a cyano-aniline 2.0g (16.95mmol), L-benzene glycinol 2.0g, with the mixture 60h that at high temperature refluxes, stopped reaction, decompression is with desolventizing,, with the residuum water dissolution, and use CHCl
3(20mLx2) extraction, the organic phase anhydrous sodium sulfate drying, the rotation desolventizing with sherwood oil/methylene dichloride (4:1) column chromatography, is volatilized thick product naturally, gets clear crystal, productive rate 30%; [a]
5 D=+67.3o (c=0.052, CH
3OH);
1HNMR (500MHz, CDCl
3, 27 ℃), δ (ppm)=7.26～7.37 (m, 4H), 5.29～5.30 (m, 1H), 4.42～4.46 (m, 1H), 4.24～4.27 (m, 1H), 2.03 (d, J=15Hz, 6H),
13CNMR 20.8,23.4, and 29.7,52.6,66.1,96.7,110.0,126.7,128.8,138.3,169.5,171.2, IR:3292,3065,2917,2849,1732,1655,1551,1455,1375,1301,1247,1041,756,701,531. HRMS (EI): m/z (%): calcd for C
12H
14O
4: 222.0892; Found:222.0883, this match crystal volume data is as follows:
Empirical formula C12H14O4
Molecular weight 222.23
Temperature 291 (2) K
Wavelength 1.54178 A
Crystallographic system, spacer rhombic system, P2 (1) P2 (1) P2 (1)
Unit cell parameters a=4.9390 (2) alpha=90 deg.
b = 9.4704(5)A beta = 90 deg
c = 26.6306 (9) A gamma = 90 deg.
Volume 1217.56 (9) A^3
Electric density 4,1.212Mg/m^3
Absorption correction parameter 0.757mm^-1
Number of electrons 472 in the unit cell
Crystallographic dimension 0.32x 0.22x 0.2mm
Scope 6.8 to 140.44 at Theta angle
Index capture range-5＜=h＜=5 of HKL ,-11＜=k＜11 ,-31＜=l＜=31
Collection/independent diffraction data 8814/ 2250 [R (int)=0.0618]
The data integrity degree 96.4% of theta=30.5
The method Multi Slice Mode of absorption correction
Transmitance 0.7386 and 0.2781 of minimax
The matrix method of least squares of the method F^2 that refine is used
Number/the number of parameters 2250/1/148 of data number/use restriction
The method 1.012 that refine is used
The consistence factor R 1=0.0654 of point diffraction, wR2=0.1217
Can observe the identical factor R 1=0.1345 of diffraction, wR2=0.1635
Absolute configuration parameter 0.33(9)
Maximum summit on the difference Fourier figure and peak valley 0.18 and-0.0.27e.A^-3
The typical bond distance's data of crystal:
| Atom | Atom | Length/ | Atom | Atom | Length/ | |
| O4 | C12 | 1.201(5) | C12 | C13 | 1.502(6) | |
| O1 | C10 | 1.335(6) | C10 | C11 | 1.465(7) | |
| O1 | C9 | 1.446(5) | C5 | C4 | 1.365(7) | |
| O3 | C8 | 1.476(5) | C5 | C6 | 1.373(7) | |
| O3 | C12 | 1.356(6) | C4 | C3 | 1.390(6) | |
| C8 | C5 | 1.492(5) | C6 | C7 | 1.383(9) | |
| C8 | C9 | 1.531(6) | C2 | C3 | 1.352(9) | |
| O2 | C10 | 1.199(6) | C2 | C7 | 1.352(9) |
The typical bond angle data of crystal:
| Atom | Atom | Atom | Angle/ | Atom | Atom | Atom | Angle/ | |
| C10 | O1 | C9 | 117.0(4) | O2 | C10 | C11 | 126.7(6) | |
| C12 | O3 | C8 | 121.2(4) | C4 | C5 | C8 | 123.8(4) | |
| O3 | C8 | C5 | 113.7(4) | C4 | C5 | C6 | 116.7(5) | |
| O3 | C8 | C9 | 108.5(4) | C6 | C5 | C8 | 119.5(5) | |
| C5 | C8 | C9 | 109.8(4) | O1 | C9 | C8 | 107.2(4) | |
| O4 | C12 | O3 | 124.2(5) | C5 | C4 | C3 | 122.0(6) | |
| O4 | C12 | C13 | 122.3(5) | C5 | C6 | C7 | 121.3(7) | |
| O3 | C12 | C13 | 113.5(4) | C7 | C2 | C3 | 119.0(6) | |
| O1 | C10 | C11 | 112.0(6) | C2 | C3 | C4 | 120.0(7) | |
| O2 | C10 | O1 | 121.3(5) | C2 | C7 | C6 | 121.0(7) |
Claims (1)
1. the synthetic method of a chipal compounds comprises synthetic, separation and purifying, it is characterized in that by the compound shown in the following chemical formula:
Cyano-aniline and chirality L-benzene glycinol have Cu (OAc) between described synthetic usefulness in chlorobenzene
2H
2When O exists under the anhydrous and oxygen-free condition back flow reaction 60 hours, Cu (OAc)
2H
2The O consumption is the 47.4mol% of material quantity, chemical name 3-carbonyl-2 (the S)-phenyl-acetic acid butyl ester of this chipal compounds.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310243718.9A CN103274936B (en) | 2013-06-19 | 2013-06-19 | Chiral compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310243718.9A CN103274936B (en) | 2013-06-19 | 2013-06-19 | Chiral compound |
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| Publication Number | Publication Date |
|---|---|
| CN103274936A true CN103274936A (en) | 2013-09-04 |
| CN103274936B CN103274936B (en) | 2014-08-06 |
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ID=49057590
Family Applications (1)
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|---|---|---|---|
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| Country | Link |
|---|---|
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996020910A1 (en) * | 1995-01-03 | 1996-07-11 | Yukong Limited | Method for optical resolution of (r,s)-1,2-phenylethanediol using enzymes |
| CN102875416A (en) * | 2012-10-31 | 2013-01-16 | 罗梅 | Chiral compound |
| CN102898342A (en) * | 2012-10-28 | 2013-01-30 | 罗梅 | Chiral compound |
-
2013
- 2013-06-19 CN CN201310243718.9A patent/CN103274936B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996020910A1 (en) * | 1995-01-03 | 1996-07-11 | Yukong Limited | Method for optical resolution of (r,s)-1,2-phenylethanediol using enzymes |
| CN102898342A (en) * | 2012-10-28 | 2013-01-30 | 罗梅 | Chiral compound |
| CN102875416A (en) * | 2012-10-31 | 2013-01-16 | 罗梅 | Chiral compound |
Non-Patent Citations (2)
| Title |
|---|
| KAMAL, A. AND G. CHOUHAN: "Chemoenzymatic synthesis of enantiomerically pure 1,2-diols employing immobilized lipase in the ionic liquid [bmim]PF6.", 《TETRAHEDRON LETTERS》 * |
| KAMAL, A., M. SANDBHOR: "hemoenzymatic synthesis of enantiomerically pure terminal 1,2-diols", 《TETRAHEDRON: ASYMMETRY》 * |
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