[ CAS No. 2483-57-0 ] {[proInfo.proName]}

Name: 2483-57-0|Methyl 2-nitroacetate|96%
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Quality Control of [ 2483-57-0 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 2483-57-0 ]

CAS No. :	2483-57-0	MDL No. :	MFCD00075480
Formula :	C₃H₅NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ALBSWLMUHHZLLR-UHFFFAOYSA-N
M.W :	119.08	Pubchem ID :	17206
Synonyms :

Calculated chemistry of [ 2483-57-0 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	25.93
TPSA :	72.12 Å²

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) :	-6.95 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.52
Log Po/w (XLOGP3) :	0.11
Log Po/w (WLOGP) :	-0.56
Log Po/w (MLOGP) :	-1.35
Log Po/w (SILICOS-IT) :	-1.77
Consensus Log Po/w :	-0.61

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.45
Solubility :	42.3 mg/ml ; 0.355 mol/l
Class :	Very soluble
Log S (Ali) :	-1.18
Solubility :	7.87 mg/ml ; 0.0661 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.31
Solubility :	241.0 mg/ml ; 2.03 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.0

Safety of [ 2483-57-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2483-57-0 ]

* 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 [ 2483-57-0 ]
Downstream synthetic route of [ 2483-57-0 ]

[ 2483-57-0 ] Synthesis Path-Upstream 1~16

1
[ 2483-57-0 ]
[ 536-74-3 ]
[ 51677-09-9 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 9, p. 2827 - 2832

2
[ 108-05-4 ]
[ 10102-43-9 ]
[ 2483-57-0 ]

Reference： [1] Patent: US4433162, 1984, A,

3
[ 108-05-4 ]
[ 2483-57-0 ]

Reference： [1] Patent: US4433162, 1984, A,

4
[ 67-56-1 ]
[ 625-75-2 ]
[ 2483-57-0 ]

Reference： [1] Chemical & Pharmaceutical Bulletin, 1984, vol. 32, # 6, p. 2200 - 2204
[2] Patent: US2557041, 1947, ,
[3] Patent: US2570297, 1946, ,
[4] Patent: US2659751, 1948, ,
[5] Justus Liebigs Annalen der Chemie, 1923, vol. 434, p. 30
[6] Patent: US2606921, 1950, ,

5
[ 29291-62-1 ]
[ 2483-57-0 ]

Reference： [1] Russian Chemical Bulletin, 1994, vol. 43, # 1, p. 70 - 74[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1994, # 1, p. 76 - 79

6
[ 6263-52-1 ]
[ 2483-57-0 ]

Reference： [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1987, vol. 36, p. 1076 - 1077[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, vol. 36, # 5, p. 1162 - 1164

7
[ 82208-51-3 ]
[ 2483-57-0 ]

8
[ 82208-51-3 ]
[ 603-35-0 ]
[ 2483-57-0 ]
[ 791-28-6 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 8, p. 1571 - 1573[2] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 8, p. 1724 - 1727

9
[ 105-45-3 ]
[ 2483-57-0 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1904, vol. <3> 31, p. 851

10
[ 186581-53-3 ]
[ 625-75-2 ]
[ 2483-57-0 ]

Reference： [1] Chemical & Pharmaceutical Bulletin, 1984, vol. 32, # 6, p. 2200 - 2204

11
[ 67-56-1 ]
[ 2483-57-0 ]

Reference： [1] Organic Process Research and Development, 2017, vol. 21, # 7, p. 1088 - 1090

12
[ 67-56-1 ]
[ 626-35-7 ]
[ 2483-57-0 ]

Reference： [1] Chirality, 2012, vol. 24, # 2, p. 112 - 118

13
[ 67-56-1 ]
[ 75-52-5 ]
[ 124-38-9 ]
[ 2483-57-0 ]

Reference： [1] Journal of Organic Chemistry, 1963, vol. 28, p. 215 - 217

14
[ 69425-55-4 ]
[ 2483-57-0 ]

Reference： [1] Bulletin des Societes Chimiques Belges, 1978, vol. 87, p. 693 - 707

15
[ 186581-53-3 ]
[ 2483-57-0 ]

Reference： [1] Chemical & Pharmaceutical Bulletin, 1984, vol. 32, # 6, p. 2200 - 2204

16
[ 64-17-5 ]
[ 53431-72-4 ]
[ 2483-57-0 ]
[ 774-48-1 ]

Reference： [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1980, vol. 29, # 3, p. 458 - 461[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1980, # 3, p. 639 - 641

[ 2483-57-0 ] Synthesis Path-Downstream 1~88

1
[ 3891-59-6 ]
[ 2483-57-0 ]
[ 62311-91-5 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1979,vol. 52,p. 2928 - 2932

2
[ 2483-57-0 ]
[ 15431-30-8 ]

Reference： [1]Helvetica Chimica Acta,2002,vol. 85,p. 4468 - 4484
[2]Tetrahedron Letters,2013,vol. 54,p. 4159 - 4163
[3]Tetrahedron Letters,1966,p. 5821 - 5822

3
[ 2483-57-0 ]
[ 762-42-5 ]
[ 69337-37-7 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 1627 - 1629
[2]Tetrahedron,2009,vol. 65,p. 2067 - 2071
[3]Journal of Organic Chemistry,2019,vol. 84,p. 13636 - 13645
[4]Bulletin of the Chemical Society of Japan,1986,vol. 59,p. 2827 - 2832
[5]Chemical and Pharmaceutical Bulletin,1980,vol. 28,p. 3296 - 3303
[6]Chemical and Pharmaceutical Bulletin,1978,vol. 26,p. 3254 - 3256

4
[ 300-57-2 ]
[ 2483-57-0 ]
methyl 5-benzyl-4,5-dihydroisoxazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With chloroamine-T In acetonitrile at 80℃;	3.2. General Procedure for the Cycloaddition of Alkenes and a-Nitroketones General procedure: Chloramine-T (0.0625 mmol, 0.5 equiv) was added to a solution of 1 (0.125 mmol,1 equiv) and 2 (0.625 mmol, 5 equiv) (or 4 (0.625 mmol, 5 equiv) or 6 (0.625 mmol, 5 equiv))in CH3CN (0.2 mL). The mixture was then stirred at 80 C until the starting materialdisappeared, as monitored by TLC. Subsequently, the mixture was directly purified byflash chromatography (with ethyl acetate/petroleum ether as the eluent) to obtain thedesired product (3, 5 or 7).
21%	With chloroformic acid ethyl ester; triethylamine In benzene for 6h; Heating;
15%	In xylene for 20h; Heating;

Reference： [1]Li, Xin; Liu, Yidi; Mao, Ying; Pan, Xinhui; Wang, Jinhui; Xin, Xiaobing; Yang, Xiaoda; Zhang, Ke; Zhao, Yanan [Molecules, 2021, vol. 26, # 12]
[2]Shimizu, Tomio; Hayashi, Yoshiyuki; Shibafuchi, Hiroshi; Teramura, Kazuhiro [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 9, p. 2827 - 2832]
[3]Shimizu; Hayashi; Teramura [Bulletin of the Chemical Society of Japan, 1984, vol. 57, # 9, p. 2531 - 2534]

5
[ 2973-09-3 ]
[ 2483-57-0 ]
5-Butyl-4,6-dioxo-4,5,6,6a-tetrahydro-3aH-pyrrolo[3,4-d]isoxazole-3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With hydroquinone In xylene for 20h; Heating;

Reference： [1]Shimizu; Hayashi; Teramura [Bulletin of the Chemical Society of Japan, 1984, vol. 57, # 9, p. 2531 - 2534]

6
[ 49619-82-1 ]
[ 2483-57-0 ]
[ 140473-25-2 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 993 - 996

7
[ 60456-77-1 ]
[ 2483-57-0 ]
[ 61973-98-6 ]

Reference： [1]Tetrahedron,1988,vol. 44,p. 2215 - 2224

8
[ 763-93-9 ]
[ 2483-57-0 ]
Methyl 3-Ethyl-2-nitro-5-oxohexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22.7%	With triethylamine In ethanol for 48h; Ambient temperature;

Reference： [1]Thompson, Wayne J.; Buhr, Chris A. [Journal of Organic Chemistry, 1983, vol. 48, # 16, p. 2769 - 2772]

9
[ 2483-57-0 ]
[ 7085-85-0 ]
2-nitro-4-cyano-1,5-pentanedioic acid 1-methyl ester 5-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With piperidine In acetonitrile at 20℃; for 24h; other CH-acids;
90%	With piperidine In acetonitrile at 20℃; for 14h;

Reference： [1]Kandror, I. I.; Galkina, M. A.; Bragina, I. O.; Lavrukhin, B. D.; Belokon', Yu. N.; Gololobov, Yu. G [Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.), 1992, vol. 41, # 10.2, p. 1928 - 1930][Izvestiya Akademi Nauk, Seriya Khimicheskaya, 1992, # 10, p. 2449 - 2452]
[2]Kandror, I. I.; Galkina, M. A.; Bragina, I. O.; Lavrukhin, B. D.; Belokon', Yu. N.; Gololobov, Yu. G [Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.), 1992, vol. 41, # 10.2, p. 1928 - 1930][Izvestiya Akademi Nauk, Seriya Khimicheskaya, 1992, # 10, p. 2449 - 2452]

10
[ 2483-57-0 ]
[ 1670-47-9 ]
[ 85093-59-0 ]

Yield	Reaction Conditions	Operation in experiment
66%	With acetic anhydride In toluene for 12h; Heating;

Reference： [1]Kochetkov, K. A.; Babievskii, K. K.; Tarbalinskaya, N. S.; Belikov, F. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1982, vol. 31, # 11, p. 2217 - 2222][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1982, # 11, p. 2515 - 2520]

11
[ 2483-57-0 ]
[ 21149-17-7 ]
[ 204922-65-6 ]

Reference： [1]Journal of the American Chemical Society,1985,vol. 107,p. 5555 - 5556
[2]Journal of the Chemical Society. Perkin transactions I,1998,p. 1113 - 1121

12
[ 2483-57-0 ]
[ 536-74-3 ]
[ 51677-09-9 ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 13636 - 13645
[2]Bulletin of the Chemical Society of Japan,1986,vol. 59,p. 2827 - 2832

13
[ 2483-57-0 ]
[ 102619-05-6 ]
3,5-bis(methoxycarbonyl)-4-<3-(1-p-toluenesulfonyl)pyrrolyl>-2-isoxazoline-2-oxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With ammonium acetate In N,N-dimethyl-formamide for 15h; Ambient temperature;

Reference： [1]Harada, Kazuho; Kaji, Eisuke; Sasaki, Kuniaki; Zen, Shonosuke [Heterocycles, 1996, vol. 42, # 1, p. 289 - 304]

14
[ 2483-57-0 ]
[ 123-11-5 ]
[ 116471-68-2 ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 3528 - 3529
[2]Journal of Organic Chemistry,2005,vol. 70,p. 8140 - 8147
[3]Journal of the American Chemical Society,2007,vol. 129,p. 1724 - 1732

15
[ 2483-57-0 ]
[ 58329-99-0 ]
(R)-Cyclohex-2-enyl-nitro-acetic acid methyl ester [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2000,vol. 39,p. 3122 - 3124

16
[ 2483-57-0 ]
[ 85217-71-6 ]
(E)-3-Methyl-2-nitro-hex-4-enoic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 6291 - 6292

17
[ 2483-57-0 ]
3-cyclopentenyl methyl carbonate [ No CAS ]
(R)-Cyclopent-2-enyl-nitro-acetic acid methyl ester [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2000,vol. 39,p. 3122 - 3124

18
[ 2483-57-0 ]
2-cycloheptenyl methyl carbonate [ No CAS ]
[ 305805-62-3 ]

Reference： [1]Angewandte Chemie - International Edition,2000,vol. 39,p. 3122 - 3124

19
[ 2483-57-0 ]
[ 459-57-4 ]
[ 666705-36-8 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 449 - 452
[2]Journal of Organic Chemistry,2005,vol. 70,p. 8140 - 8147
[3]Journal of the American Chemical Society,2007,vol. 129,p. 1724 - 1732
[4]Journal of Organic Chemistry,2007,vol. 72,p. 10088 - 10095

20
[ 2483-57-0 ]
[ 100-52-7 ]
[ 53431-72-4 ]

21
[ 2483-57-0 ]
[ 513-81-5 ]
methyl (1S,2S)-2-isopropenyl-2-methyl-1-nitrocyclopropanecarboxylate [ No CAS ]
methyl (1R,2R)-2-isopropenyl-2-methyl-1-nitrocyclopropanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With silver hexafluoroantimonate; iodosylbenzene; sodium carbonate; C25H30N2O2; copper(l) chloride; In benzene; at 20℃; for 3h;Inert atmosphere; Molecular sieve;	General procedure: CuCl (1.0 mg, 0.01 mmol, 2 mol %), AgSbF6 (4.1 mg, 0.012 mmol, 2.4 mol %), and bis(oxazoline) 2 (0.012 mmol, 2.4 mol %) were weighed in the glove box and charged together in a flask. After removal from glove box, the vial was capped and benzene (5 mL) was added. The solution was stirred for 1 h at room temperature, after which styrene (2.5 mmol, 5.0 equiv) was added to the catalyst solution. In a separate vial, PhIO (121 mg, 0.55 mmol, 1.10 equiv), Na2CO3 (122 mg, 1.15 mmol, 2.30 equiv), and molecular sieves (approx. 100 mg) were charged in a vial and purged under argon for 10 min. The solids were then quickly transferred to the catalyst solution, followed by <strong>[2483-57-0]methyl nitroacetate</strong> (1) (59.5 mg, 0.50 mmol). The solution was stirred at room temperature for 3 h. The reaction was quenched with water (5 mL) and organic layer was extracted with ethyl acetate (2×10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude oil residue was purified by flash column chromatography to give the pure 1-nitrocyclopropyl carboxylate 3.

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 18014 - 18015
[2]Tetrahedron,2012,vol. 68,p. 3487 - 3496

22
[ 623-43-8 ]
[ 2483-57-0 ]
[ 910548-27-5 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 11250 - 11259
[2]Russian Chemical Bulletin,2007,vol. 56,p. 1487 - 1494

23
[ 2483-57-0 ]
[ 67713-23-9 ]
3-(2,6-dibromo-phenyl)-2-nitro-acrylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 1724 - 1732

24
[ 2483-57-0 ]
[ 830-79-5 ]
[ 111705-26-1 ]

Yield	Reaction Conditions	Operation in experiment
66.82%	With ammonium acetate; magnesium sulfate; In dichloromethane; at 20℃; for 2h;	Example 1 :(E)-Methyl-2-nitro-3-(2,4,6-trimethoxyphenyl)acrylate; 2,4,6-trimethoxybenzaldehyde (20.75 g, 0.105 mol) was dissolved in dichloromethane (300 ml_) and to this solution magnesium sulphate (15 g, 0.124 mol), ammonium acetate (10 g, 0.129 mol) and <strong>[2483-57-0]methyl nitroacetate</strong> (12.60 g, 0.105 mol) were added and stirred at room temperature for 2 hours. At the end of two hours, water (300 ml_) was added to the reaction mass, the organic layer was separated and the aqueous layer extracted with dichloromethane (2 x 100 <n="19"/>ml_). The organic layers were combined and concentrated under reduced pressure to give a solid, which was crystallized from methanol (100 ml_). Yield: 22 g (66.82 %)1H NMR (CDCI3): delta 8.37 (s, 1 H), 6.08 (s, 2H), 3.86 (s, 3H), 3.84 (s, 3H), 3.82 (s, 6H).MS (ES+): 298 (M+1 )

Reference： [1]Patent: WO2008/7169,2008,A1 .Location in patent: Page/Page column 17-18

25
[ 2483-57-0 ]
[ 189287-30-7 ]
[ 946862-32-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1,8-diazabicyclo[5.4.0]undeca-7-ene In tetrahydrofuran at 20℃; for 72h;

Reference： [1]Powell, Amanda; Al Nakeeb, Majid; Wilkinson, Barrie; Micklefield, Jason [Chemical Communications, 2007, # 26, p. 2683 - 2685]

26
[ 20851-21-2 ]
[ 2483-57-0 ]
methyl (2RS,3SR)-3-(1H-indol-3-yl)-2-nitrobutanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26.9%	With triethylamine; In toluene; at 20℃; for 3.5h;Heating / reflux;	To a solution of N-[1-(1H-indol-3-yl)ethyl]-N-isopropylpropan-2-amine (20.23 g) in toluene (200 mL) were added <strong>[2483-57-0]methyl nitroacetate</strong> (11.91 g) and triethylamine (13.94 mL) at room temperature, and the mixture was stirred for 30 min and heated under reflux for 3 hrs. After cooling, the reaction solution was washed successively with 1N hydrochloric acid (200 mL x 3) and then water (200 mL x 2). The mixture was dried over magnesium sulfate and concentrated under reduced pressure to give a Syn/Anti mixture. To the obtained residue was added ethanol (50 mL), and the mixture was stirred at room temperature to allow precipitation of crystals. To the precipitated crystals was added hexane (100 mL), and the crystals were collected by filtration (17.68 g, yield 33.7%). The mother liquor was purified by repeating silica gel column chromatography (developing solvent; ethyl acetate/hexane=1:4-1:2) and recrystallization to give the title compound (14.09 g, yield 26.9%).

Reference： [1]Patent: EP1437351,2004,A1 .Location in patent: Page 30

27
[ 2483-57-0 ]
[ 347-54-6 ]
[ 907212-86-6 ]

Yield	Reaction Conditions	Operation in experiment
55%	With diethyl amine hydrochloride; In toluene;Heating / reflux;	[0359] 5-Fluoro-2-hydroxybenzaldehyde (7.14 g, 50.96 mmol), diethyl amine hydrochloride (6.7Og, 61.15 mmol) and <strong>[2483-57-0]methyl nitroacetate</strong> (5.62 mL, 61.15 mmol) were added together in toluene (90 mL) and stirred together at reflux under a N2 atmosphere. A Dean-Stark apparatus was fitted to the system to remove the H2O generated by the reaction. The reaction was allowed to reflux overnight, after which the mixture was cooled and diluted with H2O. The organic layer was separated, washed with brine, dried over anhydrous Na2SO4 and concentrated. Purification by flash chromatography on silica gel afforded the product as an orange solid (5.90 g, 55%)

Reference： [1]Patent: WO2006/89053,2006,A2 .Location in patent: Page/Page column 76

28
[ 2483-57-0 ]
[ 292638-85-8 ]
[ 28081-33-6 ]

Yield	Reaction Conditions	Operation in experiment
46%	With potassium carbonate; In neat (no solvent); at 90℃; for 17h;	General procedure: The nitroalkane,nitroethane (10mmol), was mixed with the Michael acceptor,methyl acrylate (10mmol). Afer through mixing, thepotassium carbonate catalyst (30mol%) was added to themixture. Heating or cooling was applied only when required, according to staring materials (Table 4). The reaction wasleft standing for the appropriate time. The catalyst was thenfiltered using a small column fitted with cotton and Florisil.The filtrate was then evaporated in vacuo and the crudeproduct was purified via column chromatography using amixture of cyclohexane and ethyl acetate afording the pure6.

Reference： [1]Russian Chemical Bulletin,2007,vol. 56,p. 1487 - 1494
[2]Journal of Chemistry,2017,vol. 2017

29
[ 2483-57-0 ]
[ 34595-26-1 ]
[ 1028090-99-4 ]
C₁₅H₁₈N₂O₄ [ No CAS ]

Reference： [1]Heterocycles,2008,vol. 75,p. 799 - 838

30
[ 2483-57-0 ]
[ 122-51-0 ]
[ 62-53-3 ]
[ 116343-89-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: orthoformic acid triethyl ester; aniline With water; acetic acid In ethanol for 0.5h; Heating / reflux; Stage #2: methyl 2-nitroacetate In ethanol; acetic acid for 3.5h; Heating / reflux; Stage #3: With hydrogenchloride; water; hydrogen; sodium hydrogencarbonate more than 3 stages;	20.A EXAMPLE 20; (αR,γS,2S)-N-((3S,4S)-3,4-dihydro-3-hydroxy-2H-1-benzopyran-4-yl)-γ-hydroxy-4-[(1-phenyl-1H-imidazol-4-yl)methyl]-α-(phenylmethyl)-2-[[(2,2,2-trifluoroethyl)amino]carbonyl]-1-piperazinepentanamide; To a solution of aniline (3.16 mL, 34.7 mmol) in ethanol (66 mL) was added acetic acid (3.5 mL), followed by triethylorthoformate (5.77 mL, 34.7 mmol). The mixture was heated to reflux for 30 min, the cooled to ambient temperature. Methyl nitroacetate (6.38 mL, 69.4 mmol) was added, and the reaction was again heated to reflux for 3.5 hours. The mixture was then cooled to 0° C., and the precipitate that formed was collected by filtration and dried in vacuo, affording 5.16 g of the nitro enamine as a white solid. This material was dissolved in triethylorthoformate (60 mL). To the solution was added 10% Pd/C (1.70 g), and the reaction was placed under 2.5 atm of H2 at 70° C. for 2 hours. The reaction was filtered through celite and concentrated in vacuo. The residue was dissolved in THF (300 mL) and cooled to 0° C., followed by addition of 1 N aqueous HCl until the solution was pH 1. After 30 min at 0° C. the solution was adjusted to pH 8 with saturated aqueous NaHCO3 and extracted with ethyl acetate (300 mL). The organic layer was washed with brine (300 mL), dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography (65% ethyl acetate in hexane) afforded the title compound as a yellow solid

Reference： [1]Current Patent Assignee: MERCK & CO INC - US6642237, 2003, B1 Location in patent: Page/Page column 115-116

31
[ 869061-79-0 ]
[ 2483-57-0 ]
[ 1073426-76-2 ]
[ 1073426-52-4 ]