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Chemical Structure| 52-90-4
Chemical Structure| 52-90-4
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Product Details of [ 52-90-4 ]

CAS No. :52-90-4 MDL No. :
Formula : C3H7NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :XUJNEKJLAYXESH-REOHCLBHSA-N
M.W : 121.16 Pubchem ID :5862
Synonyms :
Cysteine;L-Cys;Cysteinum;FEMA No. 3263;NSC 8746;(R)-Cysteine;L-(+)-Cysteine

Calculated chemistry of [ 52-90-4 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 28.94
TPSA : 102.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.37
Log Po/w (XLOGP3) : -2.49
Log Po/w (WLOGP) : -0.67
Log Po/w (MLOGP) : -3.06
Log Po/w (SILICOS-IT) : -0.69
Consensus Log Po/w : -1.31

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 1.11
Solubility : 1560.0 mg/ml ; 12.9 mol/l
Class : Highly soluble
Log S (Ali) : 0.89
Solubility : 936.0 mg/ml ; 7.73 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.59
Solubility : 470.0 mg/ml ; 3.88 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.75

Safety of [ 52-90-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P270-P264-P301+P312+P330 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 52-90-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 52-90-4 ]
  • Downstream synthetic route of [ 52-90-4 ]

[ 52-90-4 ] Synthesis Path-Upstream   1~61

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Reference: [1] Journal of Agricultural and Food Chemistry, 2001, vol. 49, # 2, p. 816 - 822
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Reference: [1] Food Chemistry, 2012, vol. 132, # 3, p. 1316 - 1323
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Reference: [1] Food Chemistry, 2012, vol. 132, # 3, p. 1316 - 1323
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Reference: [1] Journal of Agricultural and Food Chemistry, 2001, vol. 49, # 2, p. 816 - 822
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Reference: [1] Food Chemistry, 2012, vol. 132, # 3, p. 1316 - 1323
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Reference: [1] Food Chemistry, 2012, vol. 132, # 3, p. 1316 - 1323
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Reference: [1] Food Chemistry, 2010, vol. 121, # 4, p. 1060 - 1065
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Reference: [1] Food Chemistry, 2010, vol. 121, # 4, p. 1060 - 1065
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Reference: [1] Food Chemistry, 2010, vol. 121, # 4, p. 1060 - 1065
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Reference: [1] Food Chemistry, 2010, vol. 121, # 4, p. 1060 - 1065
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Reference: [1] Food Chemistry, 2010, vol. 121, # 4, p. 1060 - 1065
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Reference: [1] Food Chemistry, 2010, vol. 121, # 4, p. 1060 - 1065
  • 13
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  • [ 1708-32-3 ]
  • [ 188290-36-0 ]
  • [ 554-14-3 ]
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  • [ 74015-70-6 ]
  • [ 13623-11-5 ]
  • [ 88-15-3 ]
  • [ 24295-03-2 ]
  • [ 13679-72-6 ]
  • [ 867253-51-8 ]
Reference: [1] Food Chemistry, 2012, vol. 132, # 3, p. 1316 - 1323
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  • [ 1708-32-3 ]
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  • [ 74015-70-6 ]
  • [ 13623-11-5 ]
  • [ 88-15-3 ]
  • [ 24295-03-2 ]
  • [ 13679-72-6 ]
  • [ 867253-51-8 ]
Reference: [1] Food Chemistry, 2012, vol. 132, # 3, p. 1316 - 1323
  • 15
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  • [ 59-43-8 ]
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  • [ 63012-97-5 ]
  • [ 28588-74-1 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556
[2] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556
[3] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556
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Reference: [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556
  • 17
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Reference: [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556
  • 18
  • [ 52-90-4 ]
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Reference: [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556
  • 19
  • [ 52-90-4 ]
  • [ 624-65-7 ]
  • [ 3262-64-4 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 46, p. 5977 - 5979
  • 20
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  • [ 106-96-7 ]
  • [ 3262-64-4 ]
Reference: [1] Patent: US2757196, 1955, ,
[2] Chemical Biology and Drug Design, 2016, vol. 87, # 1, p. 101 - 111
  • 21
  • [ 52-90-4 ]
  • [ 106-95-6 ]
  • [ 21593-77-1 ]
YieldReaction ConditionsOperation in experiment
68 g
Stage #1: With sodium hydroxide In ethanol at 20℃; for 0.166667 h;
Stage #2: at 20℃; for 6 h;
(1 mol) was homogeneously dispersed in 3 L of absolute ethanol, and 3.5 mol of sodium hydroxide solution (20 mol / L) was added dropwise under magnetic stirring at room temperature and stirring was continued for 10 min. 1.1 moles of allyl bromide and reacted at room temperature for 6 h to form a crude solution of deoxythioallyl cysteine sulfoxide (2-PeCS).The solution was transferred to a clean container and adjusted to pH 5.5.4 ° C for 12 h at 30 ° C to form a white deoxy 2-PeCS crystal.(2) The 2-PeCS crystal obtained in step (1) was filtered, dried at 50 ° C, and then redissolved in 10 mL of distilled water containing 1percent glacial acetic acid and heated to boiling.The solution was poured into 150 mL of boiling ethanol and recrystallized.The solution was allowed to stand at 12 ° C for 12 h and the crystals were collected by filtration and dried at 50 ° C to give about 69 g of pure 2-PeCS.
Reference: [1] Pharmazie, 1998, vol. 53, # 10, p. 668 - 671
[2] Journal of Organic Chemistry, 1994, vol. 59, # 11, p. 3227 - 3229
[3] Organic and Biomolecular Chemistry, 2005, vol. 3, # 10, p. 2016 - 2025
[4] RSC Advances, 2016, vol. 6, # 58, p. 53519 - 53532
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 47, p. 14683 - 14687[6] Angew. Chem., 2016, vol. 128, # 47, p. 14903 - 14907,5
[7] Phytochemistry (Elsevier), 1985, vol. 24, # 7, p. 1593 - 1594
[8] Helvetica Chimica Acta, 1951, vol. 34, p. 481,486
[9] Helvetica Chimica Acta, 1948, vol. 31, p. 189,207
[10] Food and Chemical Toxicology, 2007, vol. 45, # 10, p. 2030 - 2039
[11] Patent: CN104140384, 2016, B, . Location in patent: Paragraph 0053; 0054
[12] Patent: WO2017/96450, 2017, A1, . Location in patent: Page/Page column 27
[13] Chemical Biology and Drug Design, 2016, vol. 87, # 1, p. 101 - 111
  • 22
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  • [ 107-05-1 ]
  • [ 21593-77-1 ]
Reference: [1] Patent: WO2015/8019, 2015, A1, . Location in patent: Page/Page column 82; 83
  • 23
  • [ 52-90-4 ]
  • [ 107-18-6 ]
  • [ 21593-77-1 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 6, p. 1894 - 1897
  • 24
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  • [ 556-27-4 ]
  • [ 21593-77-1 ]
YieldReaction ConditionsOperation in experiment
2.1 mg at 80℃; for 24 h; Sealed tube Aliin(Manufactured by Funakoshi Co., Ltd.) and 24.2 mg of L-cysteine (Wako Pure Chemical Industries, Ltd.) were dissolved in 10 mL of water, placed in a plastic container, sealed, kept at 80 ° C. and reacted for 24 hours . After completion of the reaction, this solution was measured using LC / TOF-MS (microTOF 2-kp manufactured by Bruker-Dartonics) to find a mass of 162.0583 as [M + H] + to produce S-allyl cysteine It was confirmed that it was doing. The content of S-allyl cysteine in the aqueous solution was analyzed by HPLC, and it was 0.28 mg / ml. Furthermore, S-allyl cysteine was purified from this aqueous solution using preparative HPLC to obtain 2.1 mg of a white powder, and its purity was analyzed by HPLC,It was 98percent
Reference: [1] Patent: JP2015/140348, 2015, A, . Location in patent: Paragraph 0032
  • 25
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Reference: [1] Phytochemistry (Elsevier), 1988, vol. 27, # 7, p. 2011 - 2016
  • 26
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  • [ 616-91-1 ]
Reference: [1] Journal of medicinal chemistry, 1968, vol. 11, # 6, p. 1176 - 1182
  • 27
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  • [ 100-39-0 ]
  • [ 3054-01-1 ]
Reference: [1] Chemical Communications, 2003, # 16, p. 2012 - 2013
[2] Organic and Biomolecular Chemistry, 2004, vol. 2, # 14, p. 2092 - 2102
[3] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 4, p. 1309 - 1315
[4] Biochemical Journal, 1936, vol. 30, p. 1598,1603
  • 28
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  • [ 100-44-7 ]
  • [ 3054-01-1 ]
Reference: [1] Journal of Biological Chemistry, 1931, vol. 94, p. 541,544
[2] Journal of Biological Chemistry, 1932, vol. 97, p. 235,240,243,246
[3] Journal of the Chemical Society [Section] C: Organic, 1970, p. 270 - 273
[4] Biological and Pharmaceutical Bulletin, 2001, vol. 24, # 11, p. 1324 - 1328
  • 29
  • [ 52-90-4 ]
  • [ 824-94-2 ]
  • [ 2544-31-2 ]
YieldReaction ConditionsOperation in experiment
64%
Stage #1: With hydrogenchloride In diethyl ether; water for 3 h;
Stage #2: With sodium hydroxide In diethyl ether; water at 20℃; for 2 h;
(Step 1)To a mixed solution of diethyl ether (400 ml) and conc. hydrochloric acid (400 ml) was added in drops 4-methoxybenzyl chloride (280 g, 1780 mmol) dissolved in diethyl ether (400 ml) for 2 h, and the mixture was stirred for 1 h. The organic layer was separated and added to a solution which was prepared by dissolving L-cysteine (197 g, 1625 mmol) and 2N aqueous sodium hydroxide solution (980 ml) in ethanol (1890 ml). The mixture was stirred for 2 h at room temperature. After completion of the reaction, the mixture was cooled to 0, and neutralized to pH 7 using 3N aqueous hydrochloric acid solution. The resulting solid was filtered and dried to give (R)-2-amino-3-(4-methoxy-benzylsulfanyl)-propionic acid (250 g, 1035 mmol, Yield 64percent).
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 11, p. 1631 - 1634
[2] Patent: US2010/291533, 2010, A1, . Location in patent: Page/Page column 22
[3] Bulletin of the Chemical Society of Japan, 1964, vol. 37, p. 433 - 434
[4] Bulletin of the Chemical Society of Japan, 1965, vol. 38, p. 120 - 123
  • 30
  • [ 52-90-4 ]
  • [ 105-13-5 ]
  • [ 2544-31-2 ]
YieldReaction ConditionsOperation in experiment
64%
Stage #1: With hydrogenchloride In diethyl ether; water for 3 h;
Stage #2: With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2 h;
Stage #3: With hydrogenchloride In diethyl ether; ethanol; water at 0℃;
4-Methoxybenzyl alcohol (280 g, 1780 mmol) dissolved in diethylether (400 mL) was added in drops to a mixture of diethylether (400 niL) and cone, hydrochloric acid (400 mL) over 2 h, and the mixture was stirred for 1 h. The organic layer was separated, and added to a solution prepared by dissolving L-cysteine (197 g, 1625 mmol) and 2N aqueous sodium hydroxide solution (980 mL) to ethanol (1890 mL).The mixture was stirred for 2 h at room temperature. After completion of the reaction, the reaction mixture was cooled to 0°C, and neutralized to pH 7 using 3N aqueous hydrochloric acid solution. The resulting solid was filtered and dried to give the title compound (250 g, Yield 64percent).
64%
Stage #1: With hydrogenchloride In diethyl ether
Stage #2: With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2 h;
Stage #3: With hydrogenchloride In diethyl ether; ethanol; water at 0℃;
4-Methoxybenzyl alcohol (280 g, 1780 mmol) dissolved in diethylether (400 mL) was added in drops to a mixture of diethylether (400 mL) and conc. hydrochloric acid (400 mL) over 2 h, and the mixture was stirred for 1 h. The organic layer was separated, and added to a solution prepared by dissolving L-cysteine (197 g, 1625 mmol) and 2N aqueous sodium hydroxide solution (980 mL) to ethanol (1890 mL). The mixture was stirred for 2 h at room temperature. After completion of the reaction, the reaction mixture was cooled to 0°, and neutralized to pH 7 using 3N aqueous hydrochloric acid solution. The resulting solid was filtered and dried to give the title compound (250 g, Yield 64percent).
64%
Stage #1: With hydrogenchloride In diethyl ether; water for 3 h;
Stage #2: With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2 h;
Stage #3: With hydrogenchloride In diethyl ether; ethanol; water
To a solvent mixture of diethylether (400 ml) and conc. hydrochloric acid (400 ml) was added in drops 4-methoxybenzylalcohol (280 g, 1780 mmol) dissolved in diethylether (400 ml) for 2 h, and the mixture was stirred for 1 h. The organic layer was separated, and added to a solution prepared by dissolving L-cysteine (197 g, 1625 mmol) and 2N aqueous sodium hydroxide solution (980 ml) in ethanol (1890 ml). The mixture was stirred for 2 h at room temperature. After completion of the reaction, the reaction solution was cooled to 0° C., and neutralized to pH 7 using 3N aqueous hydrochloric acid solution. The resulting solid was filtered, and dried to give (R)-2-amino-3-(4-methoxy-benzylsulfanyl)-propionic acid (250 g, 1035 mmol, Yield: 64percent).
Reference: [1] Patent: WO2009/25477, 2009, A1, . Location in patent: Page/Page column 65
[2] Patent: US2010/210647, 2010, A1, . Location in patent: Page/Page column 20
[3] Patent: US2010/267708, 2010, A1, . Location in patent: Page/Page column 23-24
[4] Tetrahedron Letters, 1994, vol. 35, # 11, p. 1631 - 1634
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  • [ 2544-31-2 ]
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  • [ 34317-61-8 ]
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  • 33
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  • [ 34317-61-8 ]
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  • 34
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[2] Journal of Biological Chemistry, 1931, vol. 94, p. 541,544
[3] Journal of Biological Chemistry, 1931, vol. 94, p. 541,544
  • 35
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  • [ 7732-18-5 ]
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  • 36
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  • [ 6027-13-0 ]
  • [ 56-88-2 ]
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  • 37
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  • [ 6027-13-0 ]
  • [ 56-88-2 ]
  • [ 7783-06-4 ]
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  • 38
  • [ 76-84-6 ]
  • [ 52-90-4 ]
  • [ 2799-07-7 ]
YieldReaction ConditionsOperation in experiment
90% at 20℃; for 5 h; To a solution of l-cysteine (1.0 g, 5.69 mmol) in acetic acid (15 mL) was added triphenyl methanol (1.64 g, 6.30 mmol), followed by adding trifluoroboron ethylether (720 μL, 5.69 mmol) dropwise and the reaction was stirred at room temperature. After 5 h, the reaction mixture was neutralized with saturated sodium acetate. The resulting precipitate was washed with ethylether and collected to give the desired compound 3 (1.87 g, 90percent) as a white solid. 1H NMR (300 MHz, acetone-d6): δ = 7.46-7.23 (m, 15H), 3.64 (dd, J = 8.10 Hz, 4.20 Hz, 1H), 2.67-2.52 (m, 2H). 13C NMR (75 MHz, DMSO-d6): δ = 169.89, 144.42, 129.25, 128.11, 126.78, 65.95, 53.64, 34.39. MALDI-TOF-MS: Calcd for C22H20NO2S 362.1. Found 362.1 [M-H]-.
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  • 39
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Reference: [1] Patent: WO2007/9944, 2007, A1, . Location in patent: Page/Page column 31-32
[2] Patent: WO2007/9944, 2007, A1, . Location in patent: Page/Page column 30-31
  • 40
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  • [ 1625-72-5 ]
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[2] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 7, p. 2409 - 2418
  • 41
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  • 42
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  • [ 1391926-97-8 ]
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  • [ 10312-55-7 ]
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  • 43
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  • [ 20887-95-0 ]
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  • 46
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  • 47
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  • 48
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  • [ 20887-95-0 ]
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[2] Medicinal Chemistry Research, 2017, vol. 26, # 9, p. 2180 - 2189
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  • 51
  • [ 67-56-1 ]
  • [ 52-90-4 ]
  • [ 18598-63-5 ]
YieldReaction ConditionsOperation in experiment
100% With thionyl chloride In methanol for 3 h; Reflux; Inert atmosphere General procedure: These compounds 11a-f were prepared using the generalmethod described by Gududuru et al. [35].Thionyl chloride (8.3 mL, 110 mmol) was added dropwise underan atmosphere of argon to a solution of L-cysteine (8) (9.00 g,74 mmol) in 150mL MeOH. The reaction mixture was refluxed for3 h then evaporated in vacuo, then co-evaporated with toluene(2 5 mL) to afford the hydrochloride salt of the methyl ester of Lcysteine(9) as white solid. One-sixth of this material (9)(12.4 mmol) was dissolved in water/ethanol (1:1) (15 mL). Sodiumhydrogen carbonate (1.14 g, 13.6 mmol) was added and, after10 min, the aromatic aldehyde (10a-f) (12.38 mmol) was added andthe reaction mixture was stirred for 14 h. The ethanol was evaporatedin vacuo and the aqueous residue was extracted with DCM(50 mL). The organic layer was washed with water (25 mL), driedover Na2SO4, filtered and evaporated in vacuo to afford the crudeproducts 11a-f.
96% at 0℃; for 2 h; Reflux General procedure: Acetyl chloride (1.6 mL, 22 mmol) was added to MeOH (100 mL), and the solution was cooled to 0°C. The solution was stirred for 5 min. Amino acid (L-serine, D-serine, L-cysteine, D-cysteine, L-2,3-diaminopropionic acid, and D-2,3-diaminopropionic acid) (20 mmol) was then added to the acetyl chloride solution in methanol (MeOH), and the solution was heated to reflux for 2 h, then cooled to room temperature.The reaction was evaporated under reduced pressure and gavea colorless solid. The solid was washed with CH2Cl2 (20 mL)to give amino acid methyl ester hydrochloride (2d–f, 2d–f)as a white solid. The yields of 2d, d, e, e, f and f were 95percent,96percent, 94percent, 96percent, 95percent, 95percent, respectively.
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[11] Patent: US2012/178913, 2012, A1, . Location in patent: Page/Page column 5
[12] Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1170 - 1174
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[15] Patent: CN103601742, 2016, B, . Location in patent: Paragraph 0102-0104
[16] Patent: CN105130871, 2018, B, . Location in patent: Paragraph 0038; 0042
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[2] Patent: US4745201, 1988, A,
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Reference: [1] Patent: EP1462444, 2004, A1, . Location in patent: Page 12
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  • [ 103213-32-7 ]
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  • [ 40789-98-8 ]
  • [ 67633-97-0 ]
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  • [ 28588-74-1 ]
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[3] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556
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Reference: [1] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 4, p. 1552 - 1556
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