[ CAS No. 55750-48-6 ] {[proInfo.proName]}

Name: 55750-48-6|Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate|98%
Brand: Ambeed
SKU: A126245
Price: 6.0 USD
Availability: InStock
Rating: 98 (27 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 55750-48-6

Structure of 55750-48-6 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 55750-48-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 55750-48-6 ]

SDS Specification

Alternatived Products of [ 55750-48-6 ]

Product Details of [ 55750-48-6 ]

CAS No. :	55750-48-6	MDL No. :	MFCD00042755
Formula :	C₆H₅NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LLAZQXZGAVBLRX-UHFFFAOYSA-N
M.W :	155.11	Pubchem ID :	580610
Synonyms :

Calculated chemistry of [ 55750-48-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.17
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	37.25
TPSA :	63.68 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.48 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.85
Log Po/w (XLOGP3) :	-0.33
Log Po/w (WLOGP) :	-0.7
Log Po/w (MLOGP) :	-1.16
Log Po/w (SILICOS-IT) :	-0.5
Consensus Log Po/w :	-0.37

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.46
Solubility :	53.6 mg/ml ; 0.345 mol/l
Class :	Very soluble
Log S (Ali) :	-0.55
Solubility :	44.1 mg/ml ; 0.284 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.3
Solubility :	312.0 mg/ml ; 2.01 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.43

Safety of [ 55750-48-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280	UN#:	N/A
Hazard Statements:	H302-H317	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 55750-48-6 ]

* 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 [ 55750-48-6 ]
Downstream synthetic route of [ 55750-48-6 ]

[ 55750-48-6 ] Synthesis Path-Upstream 1~4

1
[ 55750-48-6 ]
[ 141-43-5 ]
[ 1585-90-6 ]

Reference： [1] Tetrahedron Letters, 2005, vol. 46, # 7, p. 1181 - 1184
[2] Chemistry Letters, 2012, vol. 41, # 3, p. 313 - 315

2
[ 541-59-3 ]
[ 79-22-1 ]
[ 55750-48-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 4-methyl-morpholine In ethyl acetate at 0 - 20℃; for 1.5 h;	To a solution of maleimide (6.35 g, 65.4 mmol) in ethyl acetate (120 niL) at 0 °C was added NMM (8.6 niL, 78.5 mmol), followed by methyl chloroformate (6.0 mL, 78.5 mmol). The reaction was stirred at 0 °C for 30 min and r.t. 1 h. The solid was filtered off and filtrate was concentrated. The residue was dissolved in methylene chloride and filtered through a silica gel plug and eluted with methylene chloride to remove the red color. After concentration, the solid was triturated with ethyl acetate and petroleum ether to give a white solid (9.0 g, 88percent yield).
84%	Stage #1: With 4-methyl-morpholine In ethyl acetate at 0℃; for 0.166667 h; Stage #2: at 0 - 20℃; for 3 h;	To a solution of maleimide 11 (3.0 g, 31 mmol) in ethyl acetate (120 mL) was added dropwise a solution of N-methyl morpholine (4.4 mL, 40.3 mmol) in ethyl acetate (15 mL) over 10 min at 0 ^oC. Then a solution of methyl chloroformate (3.1 mL, 40.3 mmol) in ethyl acetate (8.0 mL) was added dropwise, the solution was allowed to reach room temperature while stirring for 3 h. TLC showed that the starting material was consumed completely. The solution was diluted with ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate solution, water, and saturated sodium chloride solution, successively. The organic layer was separated, dried over Na₂SO₄, and filtered. After the supernatant was concentrated under reduced pressure through rotary evaporation, the residue recrystallized from isopropyl ether to give compound 12 (4 g, 64.5 mmol, 84percent yield) as a pale solid. ¹H NMR (500 MHz, CDCl₃) δ 6.89 (s, 2H), 4.01 (s, 3H); ¹³C NMR (126 MHz, CDCl₃) δ 165.8, 148.2, 135.4, 54.4.
67%	With 4-methyl-morpholine In ethyl acetate at 0℃; for 1 h;	Example 9:conversion of an amine to a maleimide moiety /V-(Methoxycarbonyl)maleimide (37) Methyl chloroformate (0.87 ml_, 11.3 mmol) was added slowly to a solution of maleimide (1.00 g, 10.3 mmol) and /V-methyl morpholine (1.24 ml_, 1 1.3 mmol) in EtOAc (80 ml_) at 0^° C and stirred for 1 hr. The precipitate was separated out through filtration through a celite pad and the filtrate concentrated in vacuo. It was attempted to recrystallise the crude oil with hexane: CH₂CI₂ but no crystallisation occurred. The crude product was redissolved in EtOAc (100 ml_), adsorbed onto silica and purified using column chromatography (Hex: EtOAc 6:4) to yield a white solid (1 .07 g, 67percent). 5_H (CDCI₃, 300 MHz): 6.83 (2H, s, CH-3/4), 3.94 (3H, s, CH₃-2') 8c (CDCI₃, 100 MHz): 165.6 (C-2/5), 148.1 (C-1 '), 132.3 (C-3/4), 54.2 (C-2')

55%	With 4-methyl-morpholine In ethyl acetate at 0℃; for 0.5 h;	Methylchloroformate (4.4 niL, 56.7 mmol, 1 eq) was added to a solution of maleimide (5.5 g, 56.7 mmol, 1 eq) and NMM (6.2 mL, 56.7 mmol, 1 eq) in 200 niL of EtOAc at 0 ⁰C. The suspension was stirred at 0 °C for 30 minutes, filtered and washed with EtOAc. Filtrate and washings were combined and washed with cold water and dried over anhydrous Na₂SO₄. After filtration and evaporation under vacuum a pink solid was obtained. Purification by column chromatography on silica gel (Hexane-EtOAc, 1:1, v/v) provided the product (4.8 g, 55percent).
55%	With NMM In ethyl acetate	Example 1 N-(Methoxycarbonyl)maleimide (Compound 1) Methylchloroformate (4.4 mL, 56.7 mmol, 1 eq) was added to a solution of maleimide (5.5 g, 56.7 mmol, 1 eq) and NMM (6.2 mL, 56.7 mmol, 1 eq) in 200 mL of EtOAc at 0° C. The suspension was stirred at 0° C. for 30 minutes, filtered and washed with EtOAc. Filtrate and washings were combined and washed with cold water and dried over anhydrous Na₂SO₄. After filtration and evaporation under vacuum a pink solid was obtained. Purification by column chromatography on silica gel (Hexane-EtOAc, 1:1, v/v) provided the product (4.8 g, 55percent).
35%	With 4-methyl-morpholine In ethyl acetate at 0 - 20℃; for 1 h; Inert atmosphere	The title compound was prepared using a modification of the method of Foley, et al., 2010 Biomol. Chem. 8:4601-4606). To a solution of maleimide (5.0 g, 51.5 mmole) in dry ethyl acetate (250 mL) was added N-methylmorpholine (5.7 mL, 51.5 mmole) and this mixture cooled to 0° C. (ice-bath) under anhydrous N_2(g). Methyl chloroformate (4.8 mL, 61.8 mmole) was added slowly with stirring under anhydrous conditions, and the reaction allowed to stir at 0° C. for 30 min. and at room temperature for 30 min. The reaction mixture was filtered through a Buchner funnel and the white precipitate washed with ethyl acetate (100 mL). The combined filtrate was extracted with ice-water (1100 mL) and brine solution (1100 mL) and then dried over anhydrous magnesium sulfate. The product was filtered and evaporated to a clear oil that was co-evaporated with dry toluene (2*25 mL) and dried in vacuo under high vacuum overnight. The resulting clear oil was crystallized by trituration from anhydrous diethylether (50 mL) to give an off-white solid (2.77 g, 35percent) homogeneous by t.l.c. (irrigant=9:1 dichloromethane:methanol, Rf=0.62).

Reference： [1] Chemistry Letters, 2012, vol. 41, # 3, p. 313 - 315
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 20, p. 7890 - 7901
[3] Patent: WO2017/46658, 2017, A1, . Location in patent: Page/Page column 149; 150
[4] Journal of Fluorine Chemistry, 2013, vol. 152, p. 173 - 181
[5] Journal of the American Chemical Society, 2008, vol. 130, # 34, p. 11288 - 11289
[6] Organic and Biomolecular Chemistry, 2010, vol. 8, # 20, p. 4601 - 4606
[7] European Journal of Organic Chemistry, 2012, # 31, p. 6165 - 6178
[8] Angewandte Chemie - International Edition, 2018, vol. 57, # 40, p. 13216 - 13220[9] Angew. Chem., 2018, vol. 130, # 40, p. 13400 - 13404,5
[10] Patent: WO2016/46793, 2016, A2, . Location in patent: Page/Page column 55-56
[11] Patent: WO2008/34124, 2008, A2, . Location in patent: Page/Page column 70
[12] Patent: US2010/233190, 2010, A1,
[13] ChemBioChem, 2010, vol. 11, # 12, p. 1769 - 1781
[14] Organic and Biomolecular Chemistry, 2012, vol. 10, # 37, p. 7545 - 7551
[15] Organic Letters, 2015, vol. 17, # 23, p. 5846 - 5849
[16] Patent: US2018/207287, 2018, A1, . Location in patent: Paragraph 0159; 0269; 0270
[17] Journal of Medicinal Chemistry, 1997, vol. 40, # 16, p. 2643 - 2652
[18] Patent: US5091542, 1992, A,
[19] Macromolecules, 2010, vol. 43, # 14, p. 6135 - 6141
[20] Journal of Medicinal Chemistry, 2018, vol. 61, # 11, p. 4904 - 4917

3
[ 2126-93-4 ]
[ 141-78-6 ]
[ 55750-48-6 ]

Reference： [1] Patent: US2004/59101, 2004, A1,

4
[ 55750-48-6 ]
[ 110-60-1 ]
[ 28537-70-4 ]

Reference： [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 9, p. 1563 - 1572

[ 55750-48-6 ] Synthesis Path-Downstream 1~28

1
[ 55750-48-6 ]
[ 107-15-3 ]
[ 5132-30-9 ]

Yield	Reaction Conditions	Operation in experiment
64%	With sodium hydrogencarbonate In tetrahydrofuran for 3h; Ambient temperature;

Reference： [1]Cheronis, John C.; Whalley, Eric T.; Nguyen, Khe T.; Eubanks, Shad R.; Allen, Lisa G.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 9, p. 1563 - 1572]

2
[ 55750-48-6 ]
[ 57260-73-8 ]
[ 134272-63-2 ]

Yield	Reaction Conditions	Operation in experiment
92.1%	With sodium hydrogencarbonate In water at 20℃; for 1.5h; Cooling with ice;
87%	With sodium hydrogencarbonate at 0 - 20℃; for 1.5h;	40 Example 40. Synthesis of tert-butyl (2-(2,5-dioxo-2,5-dihydro-lH-pyrrol-l-yl) ethyl)carbamate (39) A mixture of tert-butyl (2-aminoethyl)carbamate (11.2 mL) and saturated NaHC03 (120 mL) was stirred vigorously at 0 °C, to which compound 38 (10.0 g, 64.4 mmol) was added in portions. After stirring at 0 °C for 30 min the reaction was warmed to r.t. and stirred for 1.0 h. The solid was then collected by vacuum filtration and then dissolved in ethyl acetate and washed with brine, dried over anhydrous Na2S04, filtered and concentrated to give a white foam (13.6 g, 87% yield).
87%	With sodium hydrogencarbonate at 0 - 20℃; for 1.5h;	115 Example 115. Synthesis of compound 419 A mixture of N-Boc-ethylenediamine (5.6 mL, 35.4 mmol, 1.1 eq. ) and saturated NaHCO3(60 mL) was cooled to 0 , to which compound 409 (5.00 g, 32.2 mmol, 1.0 eq. ) was added in portions. After stirring at 0 for 30 min, the reaction was warmed to r.t. and stirred for 1 h. The precipitate was collected by filtration and washed with cold water, then dissolved in EtOAc and washed with brine, dried over anhydrous Na2SO4and concentrated to give a white solid (6.69 g, 87%yield) .

87%	With sodium hydrogencarbonate at 0 - 20℃; for 1.5h;
87%	With sodium hydrogencarbonate at 0 - 20℃; for 1.5h;
87%	With sodium hydrogencarbonate at 0 - 20℃; for 1.5h;
87%	With sodium hydrogencarbonate In water at 0 - 20℃; for 1.5h;	115 Example 115. Synthesis of compound 419 The mixture of N-Boc-ethylenediamine (5.6 mL, 35.4 mmol) and saturated NaHCO3 (60 mL) was cooled to 0 °C, and compound 409 (5.00 g, 32.2 mmol) was added in portions. After stirring for 30 minutes at 0 °C, the reaction temperature was raised to room temperature and stirred for 1 hour. The precipitate was collected by filtration and washed with cold water, then dissolved in ethyl acetate, washed with saturated brine, dried over anhydrous Na2SO4 and concentrated to obtain a white solid (6.69 g, 87% yield).
87%	With sodium hydrogencarbonate at 0 - 20℃; for 1.5h;
78.4%	With sodium hydrogencarbonate In water at 0 - 20℃; for 0.666667h;	7 [2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)ethyl]-carbamic acid tert-butyl ester N-Boc-ethylenediamine (2.0 g, 12.48 mmol) was dissolved in a saturated solution of NaHCO3 (50 mL) and cooled to 0 °C. N-(methoxycarbonyl)maleimide (1.9 g, 12.25 mmol) was added to the stirred solution. After 10 mins the reaction mixture was diluted with water (100 mL) and stirred for 30 min at room temperature. The reaction mixture was cooled to 0° C., and the reaction mixture was filtered and washed with ice-cold water (100 mL). Drying in high vacuum afforded the title compound (2.35 g, 9.78 mmol, 78.4% yield) as a white solid. 1H NMR (500 MHz, CDCl3): δ 6.71 (s, 2H), 4.72 (s, 1H), 3.69-3.62 (m, 2H), 3.34 (d, J=5.1 Hz, 2H), 1.41 (s, 9H).
58%	With sodium hydrogencarbonate In water at 0 - 20℃;
46.8%	With sodium hydrogencarbonate at 0 - 20℃; for 1.5h;
	With sodium hydrogencarbonate at 0 - 20℃; for 1.5h;

Reference： [1]Uehara, Tomoya; Rokugawa, Takemi; Kinoshita, Mai; Nemoto, Souki; Fransisco Lazaro, Guerra Gomez; Hanaoka, Hirofumi; Arano, Yasushi [Bioconjugate Chemistry, 2014, vol. 25, # 11, p. 2038 - 2045]
[2]Current Patent Assignee: HANGZHOU DAC BIOTECH CO LTD - WO2017/46658, 2017, A1 Location in patent: Page/Page column 150
[3]Current Patent Assignee: HANGZHOU DAC BIOTECH CO LTD - WO2019/127607, 2019, A1 Location in patent: Page/Page column 12; 191
[4]Current Patent Assignee: HANGZHOU DAC BIOTECH CO LTD - WO2020/73345, 2020, A1 Location in patent: Page/Page column 180-181
[5]Current Patent Assignee: HANGZHOU DAC BIOTECH CO LTD - WO2020/155017, 2020, A1 Location in patent: Page/Page column 141; 142
[6]Current Patent Assignee: HANGZHOU DAC BIOTECH CO LTD - WO2020/257998, 2020, A1 Location in patent: Page/Page column 236
[7]Current Patent Assignee: HANGZHOU DAC BIOTECH CO LTD - TW2020/41237, 2020, A Location in patent: Paragraph 000434; 000435
[8]Current Patent Assignee: HANGZHOU DAC BIOTECH CO LTD - WO2021/212638, 2021, A1 Location in patent: Page/Page column 194
[9]Current Patent Assignee: HANGZHOU DAC BIOTECH CO LTD - US2019/125894, 2019, A1 Location in patent: Paragraph 0160-0161
[10]Location in patent: experimental part Foley, Timothy L.; Yasgar, Adam; Garcia, Christopher J.; Jadhav, Ajit; Simeonov, Anton; Burkart, Michael D. [Organic and Biomolecular Chemistry, 2010, vol. 8, # 20, p. 4601 - 4606]
[11]Arano, Yasushi; Uezono, Takashi; Akizawa, Hiromichi; Ono, Masahiro; Wakisaka, Kouji; Nakayama, Morio; Sakahara, Harumi; Konishi, Junji; Yokoyama, Akira [Journal of Medicinal Chemistry, 1996, vol. 39, # 18, p. 3451 - 3460]
[12]Han, Kenneth; Bailey, Jake B.; Zhang, Ling; Tezcan, F. Akif [Journal of the American Chemical Society, 2020, vol. 142, # 45, p. 19402 - 19410]

3
[ 541-59-3 ]
[ 79-22-1 ]
[ 55750-48-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With 4-methyl-morpholine In ethyl acetate
99%	Stage #1: maleiimide With 4-methyl-morpholine In ethyl acetate at 0℃; for 0.166667h; Stage #2: methyl chloroformate In ethyl acetate at 20℃; for 1h;	1.1 1) Preparation of M3: Add maleimide (M1, 4.0g, 41.2mmol) to a 500mL three-necked flask,Dissolved in ethyl acetate (EA, 160mL), then placed in ice water to cool to 0 ° C,A solution of N-methylmorpholine (NMM; 3.7g, 41mmol) in EA (20mL) was slowly added dropwise,After stirring for 10 min, continue to slowly add methyl chloroformate (M2, 4.92 g, 40 mmol) in EA (10 mL) solution. After the dropwise addition, slowly warm to room temperature to continue the reaction for 1 h.After the reaction, the insoluble salt was removed by filtration, and the filtrate was concentrated to obtain the crude product as a red oil.After standing at a low temperature, a purple-red crystalline solid (6.55 g, 99% yield) precipitated.The nature of this product is unstable, and the next reaction is carried out without further purification.
98%	With 4-methyl-morpholine In ethyl acetate at 0℃; for 0.5h;

89%	With 4-methyl-morpholine In ethyl acetate at 0 - 20℃; for 1.5h;	108 Example 108. Synthesis of compound 409 To a solution of maleimide (6.35 g, 65.4 mmol, 1.0 eq. ) in EtOAc (120 mL) were added N-methyl morpholine (8.6 mL, 78.5 mmol, 1.2 eq. ) and methyl chloroformate (6.0 mL, 78.5 mmol, 1.2 eq. ) at 0 . The reaction was stirred at 0 for 30 min and r.t. 1 h. The solid was filtered off and filtrate concentrated. The residue was dissolved in CH2Cl2and filtered through a silica gel plug and eluated with CH2Cl2to remove the color. The appropriate fractions were concentrated and resulted solid was triturated with 10%EtOAc/PE to give a white solid (9.00 g, 89%yield) .
89%	With 4-methyl-morpholine In ethyl acetate at 0 - 20℃; for 1.5h;
88%	With 4-methyl-morpholine In ethyl acetate
88%	With 4-methyl-morpholine In ethyl acetate at 0 - 20℃; for 1.5h;	39 Example 39. Synthesis of methyl 2,5-dioxo-2,5-dihydro-lH-pyrrole-l- carboxylate (38) To a solution of maleimide (6.35 g, 65.4 mmol) in ethyl acetate (120 niL) at 0 °C was added NMM (8.6 niL, 78.5 mmol), followed by methyl chloroformate (6.0 mL, 78.5 mmol). The reaction was stirred at 0 °C for 30 min and r.t. 1 h. The solid was filtered off and filtrate was concentrated. The residue was dissolved in methylene chloride and filtered through a silica gel plug and eluted with methylene chloride to remove the red color. After concentration, the solid was triturated with ethyl acetate and petroleum ether to give a white solid (9.0 g, 88% yield).
84%	Stage #1: maleiimide With 4-methyl-morpholine In ethyl acetate at 0℃; for 0.166667h; Stage #2: methyl chloroformate In ethyl acetate at 0 - 20℃; for 3h;	Methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate 12 To a solution of maleimide 11 (3.0 g, 31 mmol) in ethyl acetate (120 mL) was added dropwise a solution of N-methyl morpholine (4.4 mL, 40.3 mmol) in ethyl acetate (15 mL) over 10 min at 0 oC. Then a solution of methyl chloroformate (3.1 mL, 40.3 mmol) in ethyl acetate (8.0 mL) was added dropwise, the solution was allowed to reach room temperature while stirring for 3 h. TLC showed that the starting material was consumed completely. The solution was diluted with ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate solution, water, and saturated sodium chloride solution, successively. The organic layer was separated, dried over Na2SO4, and filtered. After the supernatant was concentrated under reduced pressure through rotary evaporation, the residue recrystallized from isopropyl ether to give compound 12 (4 g, 64.5 mmol, 84% yield) as a pale solid. 1H NMR (500 MHz, CDCl3) δ 6.89 (s, 2H), 4.01 (s, 3H); 13C NMR (126 MHz, CDCl3) δ 165.8, 148.2, 135.4, 54.4.
83%	With 4-methyl-morpholine In ethyl acetate at 0℃; for 0.5h;
82.9%	With 4-methyl-morpholine In ethyl acetate at 0 - 20℃; for 2.25h;	6 2,5-Dioxo-2,5-dihydro-pyrrole-1-carboxylic acid methyl ester Maleimide (12.0 g, 123.7 mmol) was dissolved in ethyl acetate (150 mL) in a 250 mL round-bottom flask, and the solution was cooled to approximately 0 °C. A solution of N-methyl morpholine, (14.1 mL, 12.8 g, 126.2 mmol) in ethyl acetate (10 mL) was added dropwise over 15 min. A solution of methyl chloroformate (9.60 mL, 11.5 g, 123.7 mmol) in ethyl acetate (50 mL) was added dropwise, and the solution was warmed to room temperature and stirring for 2 h. The solution was diluted with ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate solution, water, and saturated sodium chloride solution. The organic layer was separated, dried over Na2SO4, and filtered. The supernatant was concentrated under reduced pressure to yield the title compound as a solid (15.9 g, 102.5 mmol, 82.9% yield). 1H NMR (500 MHz, CDCl3): δ 6.84 (s, 2H), 3.97 (s, 3H).
81%	With 4-methyl-morpholine In ethyl acetate at 0 - 20℃; for 1h;
78%	With 4-methyl-morpholine In ethyl acetate Cooling with ice; Inert atmosphere;
78%	With 4-methyl-morpholine In ethyl acetate at 0 - 3℃; for 0.5h; Inert atmosphere;
74%	With 4-methyl-morpholine In ethyl acetate at 0 - 20℃; for 1.5h;
67%	With 4-methyl-morpholine In ethyl acetate at 0℃; for 1h;	9 /V-(Methoxycarbonyl)maleimide (37) Example 9:conversion of an amine to a maleimide moiety /V-(Methoxycarbonyl)maleimide (37) Methyl chloroformate (0.87 ml_, 11.3 mmol) was added slowly to a solution of maleimide (1.00 g, 10.3 mmol) and /V-methyl morpholine (1.24 ml_, 1 1.3 mmol) in EtOAc (80 ml_) at 0° C and stirred for 1 hr. The precipitate was separated out through filtration through a celite pad and the filtrate concentrated in vacuo. It was attempted to recrystallise the crude oil with hexane: CH2CI2 but no crystallisation occurred. The crude product was redissolved in EtOAc (100 ml_), adsorbed onto silica and purified using column chromatography (Hex: EtOAc 6:4) to yield a white solid (1 .07 g, 67%). 5H (CDCI3, 300 MHz): 6.83 (2H, s, CH-3/4), 3.94 (3H, s, CH3-2') 8c (CDCI3, 100 MHz): 165.6 (C-2/5), 148.1 (C-1 '), 132.3 (C-3/4), 54.2 (C-2')
55%	With 4-methyl-morpholine In ethyl acetate at 0℃; for 0.5h;	1 Methylchloroformate (4.4 niL, 56.7 mmol, 1 eq) was added to a solution of maleimide (5.5 g, 56.7 mmol, 1 eq) and NMM (6.2 mL, 56.7 mmol, 1 eq) in 200 niL of EtOAc at 0 0C. The suspension was stirred at 0 °C for 30 minutes, filtered and washed with EtOAc. Filtrate and washings were combined and washed with cold water and dried over anhydrous Na2SO4. After filtration and evaporation under vacuum a pink solid was obtained. Purification by column chromatography on silica gel (Hexane-EtOAc, 1:1, v/v) provided the product (4.8 g, 55%).
55%	With NMM In ethyl acetate	1 N-(Methoxycarbonyl)maleimide (Compound 1) Example 1 N-(Methoxycarbonyl)maleimide (Compound 1) Methylchloroformate (4.4 mL, 56.7 mmol, 1 eq) was added to a solution of maleimide (5.5 g, 56.7 mmol, 1 eq) and NMM (6.2 mL, 56.7 mmol, 1 eq) in 200 mL of EtOAc at 0° C. The suspension was stirred at 0° C. for 30 minutes, filtered and washed with EtOAc. Filtrate and washings were combined and washed with cold water and dried over anhydrous Na2SO4. After filtration and evaporation under vacuum a pink solid was obtained. Purification by column chromatography on silica gel (Hexane-EtOAc, 1:1, v/v) provided the product (4.8 g, 55%).
52%	With 4-methyl-morpholine In ethyl acetate at 0℃; for 2h;
52%	Stage #1: maleiimide With 4-methyl-morpholine In ethyl acetate at 0℃; for 0.166667h; Stage #2: methyl chloroformate In ethyl acetate at 20℃; for 2h; Inert atmosphere;
48%	With triethylamine In dichloromethane at 20℃; for 0.416667h;
35%	With 4-methyl-morpholine In ethyl acetate at 0 - 20℃; for 1h; Inert atmosphere;	2 N-(Methoxycarbonyl)-maleimide (M1970) The title compound was prepared using a modification of the method of Foley, et al., 2010 Biomol. Chem. 8:4601-4606). To a solution of maleimide (5.0 g, 51.5 mmole) in dry ethyl acetate (250 mL) was added N-methylmorpholine (5.7 mL, 51.5 mmole) and this mixture cooled to 0° C. (ice-bath) under anhydrous N2(g). Methyl chloroformate (4.8 mL, 61.8 mmole) was added slowly with stirring under anhydrous conditions, and the reaction allowed to stir at 0° C. for 30 min. and at room temperature for 30 min. The reaction mixture was filtered through a Buchner funnel and the white precipitate washed with ethyl acetate (100 mL). The combined filtrate was extracted with ice-water (1100 mL) and brine solution (1100 mL) and then dried over anhydrous magnesium sulfate. The product was filtered and evaporated to a clear oil that was co-evaporated with dry toluene (2*25 mL) and dried in vacuo under high vacuum overnight. The resulting clear oil was crystallized by trituration from anhydrous diethylether (50 mL) to give an off-white solid (2.77 g, 35%) homogeneous by t.l.c. (irrigant=9:1 dichloromethane:methanol, Rf=0.62).
	With 4-methyl-morpholine
	With 4-methyl-morpholine In ethyl acetate	1 Preparation of N-Methoxycarbonylmaleimide STR13 Example 1 Preparation of N-Methoxycarbonylmaleimide STR13 To a 1000 ml 3-neck round bottom flask was added 400 ml of ethyl acetate. The flask was placed in an ice bath and the temperature was allowed to drop to about 0° C. To the cooled flask was sequentially added with stirring 7.76 g of maleimide and 8.8 ml of N-methylmorpholine. Then, through an addition funnel was added to the stirring mixture 6.26 ml of methyl chloroformate at a rate so as not to raise the temperature above 3° C. Through the addition funnel was then added 5 ml of ethyl acetate as washing and the washing was added to the reaction mixture. The reaction mixture was stirred for 30 minutes at between 0°-3° C. Thereafter, the reaction mixture was filtered through a Buchner funnel. The flask was washed 2* with 10 ml of ethyl acetate and the washings were also filtered. The resulting precipitate was washed 2*with 10 ml of ethyl acetate. The combined filtrate and washings were extracted with 100 ml of ice cold water, dried (10 g Na2 SO4), and evaporated to dryness under reduced pressure.
	With 4-methyl-morpholine In ethyl acetate at 0℃; for 0.5h;
	at 0 - 20℃; for 1h;
	Stage #1: maleiimide With 4-methyl-morpholine In ethyl acetate at 0℃; for 0.166667h; Stage #2: methyl chloroformate In ethyl acetate at 20℃;

Reference： [1]Fujita, Daishi; Suzuki, Kosuke; Sato, Sota; Yagi-Utsumi, Maho; Kurimoto, Eiji; Yamaguchi, Yoshiki; Kato, Koichi; Fujita, Makoto [Chemistry Letters, 2012, vol. 41, # 3, p. 313 - 315]
[2]Current Patent Assignee: INST MILITARY MEDICINE ACADEMY MILITARY SCIENCES PLA - CN110759940, 2020, A Location in patent: Paragraph 0171-0173; 0183-0186
[3]Wang, Meng; Bao, Wei-Wei; Chang, Wen-Ying; Chen, Xu-Man; Lin, Bao-Ping; Yang, Hong; Chen, Er-Qiang [Macromolecules, 2019, vol. 52, # 15, p. 5791 - 5800]
[4]Current Patent Assignee: HANGZHOU DAC BIOTECH CO LTD - WO2019/127607, 2019, A1 Location in patent: Page/Page column 12; 189
[5]Current Patent Assignee: HANGZHOU DAC BIOTECH CO LTD - WO2020/73345, 2020, A1 Location in patent: Page/Page column 180
[6]Harada, Naoya; Kimura, Hiroyuki; Ono, Masahiro; Saji, Hideo [Journal of Medicinal Chemistry, 2013, vol. 56, # 20, p. 7890 - 7901]
[7]Current Patent Assignee: HANGZHOU DAC BIOTECH CO LTD - WO2017/46658, 2017, A1 Location in patent: Page/Page column 149; 150
[8]Yue, Xuyi; Feng, Yue; Yu, Y. Bruce [Journal of Fluorine Chemistry, 2013, vol. 152, p. 173 - 181]
[9]Han, Kenneth; Bailey, Jake B.; Zhang, Ling; Tezcan, F. Akif [Journal of the American Chemical Society, 2020, vol. 142, # 45, p. 19402 - 19410]
[10]Current Patent Assignee: HANGZHOU DAC BIOTECH CO LTD - US2019/125894, 2019, A1 Location in patent: Paragraph 0158-0159
[11]De, Priyadarsi; Li, Ming; Gondi, Sudershan R.; Sumerlin, Brent S. [Journal of the American Chemical Society, 2008, vol. 130, # 34, p. 11288 - 11289]
[12]Location in patent: experimental part Foley, Timothy L.; Yasgar, Adam; Garcia, Christopher J.; Jadhav, Ajit; Simeonov, Anton; Burkart, Michael D. [Organic and Biomolecular Chemistry, 2010, vol. 8, # 20, p. 4601 - 4606]
[13]Villemin, Elise; Herent, Marie-France; Marchand-Brynaert, Jacqueline [European Journal of Organic Chemistry, 2012, # 31, p. 6165 - 6178]
[14]Hammer, Niels; Erickson, Jeremy D.; Lauridsen, Vibeke H.; Jakobsen, Joakim B.; Hansen, Bente K.; Jacobsen, Kristian M.; Poulsen, Thomas B.; Jørgensen, Karl Anker [Angewandte Chemie - International Edition, 2018, vol. 57, # 40, p. 13216 - 13220][Angew. Chem., 2018, vol. 130, # 40, p. 13400 - 13404,5]
[15]Current Patent Assignee: SOUTH AFRICAN NUCLEAR ENERGY CORP LTD; UNIVERSITY OF CAPE TOWN - WO2016/46793, 2016, A2 Location in patent: Page/Page column 55-56
[16]Current Patent Assignee: BELROSE PHARMA INC - WO2008/34124, 2008, A2 Location in patent: Page/Page column 70
[17]Current Patent Assignee: BELROSE PHARMA INC - US2010/233190, 2010, A1
[18]Location in patent: experimental part Willems, Lianne I.; Verdoes, Martijn; Florea, Bogdan I.; Van Der Marel, Gijsbert A.; Overkleeft, Herman S. [ChemBioChem, 2010, vol. 11, # 12, p. 1769 - 1781]
[19]O'Connell, Kieron M. G.; Beckmann, Henning S. G.; Laraia, Luca; Horsley, Helen T.; Bender, Andreas; Venkitaraman, Ashok R.; Spring, David R. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 37, p. 7545 - 7551]
[20]Sengoku, Tetsuya; Murata, Yusuke; Aso, Yuwa; Kawakami, Ai; Inuzuka, Toshiyasu; Sakamoto, Masami; Takahashi, Masaki; Yoda, Hidemi [Organic Letters, 2015, vol. 17, # 23, p. 5846 - 5849]
[21]Current Patent Assignee: ABCAM PLC - US2018/207287, 2018, A1 Location in patent: Paragraph 0159; 0269; 0270
[22]Wakisaka, Kouji; Arano, Yasushi; Uezono, Takashi; Akizawa, Hiromichi; Ono, Masahiro; Kawai, Keiichi; Ohomomo, Yoshiro; Nakayama, Morio; Saji, Hideo [Journal of Medicinal Chemistry, 1997, vol. 40, # 16, p. 2643 - 2652]
[23]Current Patent Assignee: DANAHER CORP - US5091542, 1992, A
[24]Location in patent: scheme or table Swanson, John P.; Rozvadovsky, Svetlana; Seppala, Jonathan E.; MacKay, Michael E.; Jensen, Robert E.; Costanzo, Philip J. [Macromolecules, 2010, vol. 43, # 14, p. 6135 - 6141]
[25]Zhang, Huicong; Wang, Kuanglei; Na, Kexin; Li, Dan; Li, Zhenbao; Zhao, Dongyang; Zhong, Lu; Wang, Menglin; Kou, Longfa; Luo, Cong; Zhang, Haotian; Kan, Qiming; Ding, Huaiwei; He, Zhonggui; Sun, Jin [Journal of Medicinal Chemistry, 2018, vol. 61, # 11, p. 4904 - 4917]
[26]Wang, Yanming; Fan, Shiyong; Xiao, Dian; Xie, Fei; Li, Wei; Zhong, Wu; Zhou, Xinbo [Cancers, 2019, vol. 11, # 7]

4
[ 55750-48-6 ]
[ 106719-44-2 ]
N^ε-maleoyl-α-(tert-butyloxycarbonyl)-D-lysine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2643 - 2652

5
[ 55750-48-6 ]
[ 4048-33-3 ]
[ 157503-18-9 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium hydrogencarbonate In water at 0 - 25℃;
75%	With sodium hydrogencarbonate at 0 - 25℃;
55%	With sodium hydrogencarbonate In water at 0 - 20℃; for 0.833333h; Inert atmosphere;

52%	With sodium hydrogencarbonate In water at 0℃; for 2h;
	With sodium hydrogencarbonate In water at 0℃; Inert atmosphere;
	With sodium hydrogencarbonate In water at 0℃; for 1.5h;	34.1 Step 1 : To a 100 mL round bottom flask was added 6-amino-1 -hexanol (1 .00g, 6.44 mmol) in saturated NaHC03aqueous solution (12.0 mL). The mixture was cooled at 0°C, and N- methoxycarbonylmaleimide (0.750 g, 6.44 mmol) was added. The reaction mixture was stirred at 0°C for 1 .5 hours. Then the reaction mixture was acidified at 0°C with 2 M HCI to pH1 . The acidified reaction mixture was extracted with ethyl acetate (AcOEt). The organic layer was concentrated. The residue was dissolved in DCM, loaded onto a silica gel column, and eluted with MeOH/DCM (0-4%) to obtain 1 -(6-hydroxyhexyl)-1 H-pyrrole- 2,5-dione as white solid, MS m/z 198.2 (M+1 ).1H NMR (400 MHz, CDCI3): δ 6.68 (s, 2H), 3.63 (t, d = 6.4 Hz, 2H), 3.52 (t, d = 7.2 Hz, 2H), 1 .63-1 .52 (m, 4H), 1 .43-1 .28 (m, 4H).
	With sodium hydrogencarbonate In water at 0℃; for 1.5h;	3-34.1 Step 1: To a 100 mL round bottom flask was added 6-amino-1-hexanol (1.OOg, 6.44mmol) in saturated NaHCO3 aqueous solution (12.0 mL). The mixture was cooled at 0°C, and Nmethoxycarbonylmaleimide (0.750 g, 6.44 mmol) was added. The reaction mixture was stirred at 0°C for1.5 hours. Then the reaction mixture was acidified at 0°C with 2 M HC1 to pHi. The acidified reaction mixture was extracted with ethyl acetate (AcOEt). The organic layer was concentrated. The residue was dissolved in DCM, loaded onto a silica gel column, and eluted with MeOH/DCM (0-4%) to obtain 1-(6- hydroxyhexyl)-1H-pyrrole-2,5-dione as white solid, MS m/z 198.2 (M+1). ‘H NMR (400 MHz, CDC13): ö 6.68 (s, 2H), 3.63 (t, d = 6.4 Hz, 2H), 3.52 (t, d = 7.2 Hz, 2H), 1.63-1.52 (m, 4H), 1.43-1.28 (m, 4H).

Reference： [1]Constant, Céline; Albert, Steeve; Zivic, Nicolas; Baczko, Krystyna; Fensterbank, Hélène; Allard, Emmanuel [Tetrahedron, 2014, vol. 70, # 18, p. 3023 - 3029]
[2]Keller, Keith A.; Guo, Jianhua; Punna, Sreenivas; Finn [Tetrahedron Letters, 2005, vol. 46, # 7, p. 1181 - 1184]
[3]Villemin, Elise; Herent, Marie-France; Marchand-Brynaert, Jacqueline [European Journal of Organic Chemistry, 2012, # 31, p. 6165 - 6178]
[4]Wang, Meng; Bao, Wei-Wei; Chang, Wen-Ying; Chen, Xu-Man; Lin, Bao-Ping; Yang, Hong; Chen, Er-Qiang [Macromolecules, 2019, vol. 52, # 15, p. 5791 - 5800]
[5]Hammaecher, Catherine; Joris, Bernard; Goormaghtigh, Erik; Marchand-Brynaert, Jacqueline [European Journal of Organic Chemistry, 2013, # 35, p. 7952 - 7959]
[6]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2015/95301, 2015, A2 Location in patent: Page/Page column 111
[7]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2016/203432, 2016, A1 Location in patent: Paragraph 00493; 00494

6
[ 55750-48-6 ]
[ 141-43-5 ]
[ 1585-90-6 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 1181 - 1184
[2]Chemistry Letters,2012,vol. 41,p. 313 - 315

7
[ 55750-48-6 ]
[ 134272-63-2 ]

Yield	Reaction Conditions	Operation in experiment
	In water	b b) To this solution was added 0.78 g of N-methoxycarbonylmaleimide (5.0 mmoles, 100 mol%). The heterogeneous mixture was stirred vigorously for 20 min at 0°, followed by 1 h at room temperature. Water (50 ml) was added and the mixture extracted with chloroform (2*50 ml). The extracts were dried over Na2 SO4, filtered and the solvent removed to give a white solid. This solid was purified by chromatography on silica gel, eluding with an EtOAc/hexanes gradient. NMR (300 MHz, DMSO-d6) δ1.33 (s,9H), 3.05 (m, 2H), 3.42 (m, 2H), 7.01 (s, 2H).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US5180816, 1993, A

8
[ 55750-48-6 ]
[ 183896-00-6 ]
[ 183896-02-8 ]

Yield	Reaction Conditions	Operation in experiment
49%	With sodium hydrogencarbonate In water at 0 - 20℃; for 0.416667h;	9 EXAMPLE 9; Method for Preparing a Water-soluble Biotinylation Regent that is Reactive with Sulfhydryls or Amines Biotin-4,7,10-trioxa-1,13-tridecanediamine (1.0 g, 2.2 mmol) was dissolved in 12 mL of saturated aqueous sodium bicarbonate and cooled with ice water. N-methoxycarbonyl-maleimide (4.5 mmol, 0.696 g) was added and the reaction stirred at 0° C. for 10 minutes. A 50 mL quantity of water was added to the reaction and the stirring was continued at room temperature for an additional 15 minutes. The solution was extracted with (4×100 mL) chloroform. The combined chloroform extracts were washed with (2×50 mL) water, dried over anhydrous sodium sulfate, and chloroform removed under vacuum. The product was triturated in 100 mL ether and filtered. The isolated product was dried under vacuum to yield 0.57 g (49%) of the compound 18 as a colorless solid; mp=112-114° C.; 1H NMR (MeOH, δ): 1.46 (m, 2H), 1.6-1.8 (m, 9H), 2.2 (t, 2H), 2.7 (d, 1H), 2.9 (dd, 1H), 3.2-3.3 (m, 4H), 3.5-3.6 (m, 15H), 4.3 (m, 1H), 4.5 (m, 1H), 6.8 (s, 2H); IR (KBr, cm-1): 3280, 2910, 2850, 1760, 1690, 1640, 1110, 940; HRMS: calculated for C24H38N4O7S (M+H) is 527.2539, found 527.2526.

Reference： [1]Current Patent Assignee: QUANTA BIODESIGN - US2006/228325, 2006, A1 Location in patent: Page/Page column 36

9
[ 55750-48-6 ]
[ 1091627-77-8 ]
[ 1292268-22-4 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 1641 - 1644

10
[ 55750-48-6 ]
[ 180683-64-1 ]
[ 1332702-03-0 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 14704 - 14709

11
[ 55750-48-6 ]
[ 2508-29-4 ]
1-(5-hydroxypentyl)-1H-pyrrole-2,5-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydrogencarbonate In water at 0℃; for 1.5h;	20.1 Example 2 0-1. Synthesis of maleimide alcohol derivative (47) To a cooled (0 °C) solution of 5-aminopentan-1-ol (100 mg, 0.97 tmol) in saturated aqueous NaHCO3 (16 mL) was added N-methoxycarbonylmaleimide (150 mg, 0.64 tmol). The mixture was stirred for 1.5 h and extracted with DCM (2 x 20 mL). Thecombined organic layers were dried (Na2SO4) and concentrated. The product 47 was obtained as a colorless oil (137 mg, 0.75 mmol, 75%). ‘H NIVIR (400 MHz, CDC13) (ppm) 6.69 (s, 2H), 3.70-3.67 (m, 1H), 3.67-3.60 (m, 2H), 3.53 (t, J 7.1 Hz, 2H), 1.68- 1.54 (m, 4H), 1.42-1.31 (m, 2H).
60%	With sodium hydrogencarbonate In water at 0 - 20℃; for 0.833333h; Inert atmosphere;
53%	With sodium hydrogencarbonate In water at 0 - 20℃; for 0.833333h; Inert atmosphere;

48.2%	With sodium hydrogencarbonate at 0 - 20℃; for 2h; Inert atmosphere;
	With sodium hydrogencarbonate In water at 0 - 20℃; for 0.833333h;

Reference： [1]Current Patent Assignee: SYNAFFIX BV - WO2016/53107, 2016, A1 Location in patent: Page/Page column 98
[2]Hammaecher, Catherine; Joris, Bernard; Goormaghtigh, Erik; Marchand-Brynaert, Jacqueline [European Journal of Organic Chemistry, 2013, # 35, p. 7952 - 7959]
[3]Villemin, Elise; Herent, Marie-France; Marchand-Brynaert, Jacqueline [European Journal of Organic Chemistry, 2012, # 31, p. 6165 - 6178]
[4]Finniss, Mathew C.; Chu, Kevin S.; Bowerman, Charles J.; Luft, J. Christopher; Haroon, Zishan A.; Desimone, Joseph M. [MedChemComm, 2014, vol. 5, # 9, p. 1355 - 1358]
[5]Zhang, Huicong; Wang, Kuanglei; Na, Kexin; Li, Dan; Li, Zhenbao; Zhao, Dongyang; Zhong, Lu; Wang, Menglin; Kou, Longfa; Luo, Cong; Zhang, Haotian; Kan, Qiming; Ding, Huaiwei; He, Zhonggui; Sun, Jin [Journal of Medicinal Chemistry, 2018, vol. 61, # 11, p. 4904 - 4917]

12
[ 55750-48-6 ]
[ 1404072-05-4 ]
[ 518044-40-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydrogencarbonate at 0 - 20℃; for 1.66667h;	3-(2-{2-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethoxy]ethoxy}ethoxy)propanoic acid 186 mg (555 μmol) of 3-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}propanoic acid trifluoroacetate were dissolved in 2.6 ml of saturated sodium hydrogencarbonate solution and admixed at 0° C. with 86 mg (555 μmol) of N-methoxycarbonylmaleimide. The reaction mixture was stirred at 0° C. for 40 min and at RT for 1 h, then cooled again to 0° C., adjusted to pH 3 with sulphuric acid and extracted 3× with 25 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated. [1548] 126 mg (75% of theory) of the title compound were obtained. [1549] LC-MS (Method 1): Rt=0.53 min; m/z=302 (M+H)+
75%	With sodium hydrogencarbonate at 0 - 20℃; for 1.66667h;	42 3-(2-{ 2-[2-(2,5-dioxo-2,5-dihydro-1 H -pyrrol-1-yl)ethoxy ]ethoxy }ethoxy)propanoic acid [3921] 186 mg (555 f.tmol) of 3-{2-[2-(2-aminoethoxyl)ethoxy ]ethoxy }propanoic acid trifluoroacetate were dissolvedin 2.6 ml of saturated sodiumhydrogencarbonate solutionand admixed at oo C. with 86 mg (555 f.tmol) ofN-methoxycarbonylmaleimide. The reaction mixture wasstirred at oo C. for 40 min and at RT for 1 h, then cooled againto oo C., adjusted to pH 3 with sulphuric acid and extracted 3xwith 25 ml of ethyl acetate. The combined organic phaseswere dried over magnesium sulphate and concentrated. 126mg (75% of theory) of the title compound were obtained.[3922] LC-MS (Method 1): R,=0.53 min; m/z=302(M+Ht.
		3-(2-{2-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethoxy]ethoxy}ethoxy)propanoic acid 3-(2-{2-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethoxy]ethoxy}ethoxy)propanoic acid 186 mg (555 μmol) of 3-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}propanoic acid trifluoroacetate were dissolved in 2.6 ml of saturated sodium hydrogencarbonate solution and admixed at 0° C. with 86 mg (555 μmol) of N-methoxycarbonylmaleimide. The reaction mixture was stirred at 0° C. for 40 min and at RT for 1 h, then cooled again to 0° C., adjusted to pH 3 with sulphuric acid and extracted 3* with 25 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated. 126 mg (75% of theory) of the title compound were obtained. LC-MS (Method 1): Rt=0.53 min; m/z=302 (M+H)+.

Reference： [1]Current Patent Assignee: SEAGEN INC - US2015/23989, 2015, A1 Location in patent: Paragraph 1547-1549
[2]Current Patent Assignee: SEAGEN INC - US2015/246136, 2015, A1 Location in patent: Paragraph 3920-3922
[3]Current Patent Assignee: SEAGEN INC - US2013/66055, 2013, A1 Location in patent: Page/Page column Current Patent Assignee: SEAGEN INC - US2014/127240, 2014, A1 Location in patent: Page/Page column

13
[ 55750-48-6 ]
[ 1013921-36-2 ]
[ 1262681-30-0 ]

Yield	Reaction Conditions	Operation in experiment
49%	With sodium hydrogencarbonate In water at 0 - 20℃; for 2h;

Reference： [1]Goswami, Lalit N.; Houston, Zachary H.; Sarma, Saurav J.; Jalisatgi, Satish S.; Hawthorne, M. Frederick [Organic and Biomolecular Chemistry, 2013, vol. 11, # 7, p. 1116 - 1126]

14
[ 55750-48-6 ]
[ 39160-70-8 ]
1-{2-[2-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethyl}pyrrole-2,5-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With sodium hydrogencarbonate In water at 0 - 20℃; for 0.833333h; Inert atmosphere;

Reference： [1]Hammaecher, Catherine; Joris, Bernard; Goormaghtigh, Erik; Marchand-Brynaert, Jacqueline [European Journal of Organic Chemistry, 2013, # 35, p. 7952 - 7959]

15
[ 55750-48-6 ]
[ 34188-11-9 ]
1-(2-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethyl)pyrrole-2,5-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 24h;

Reference： [1]Hammaecher, Catherine; Joris, Bernard; Goormaghtigh, Erik; Marchand-Brynaert, Jacqueline [European Journal of Organic Chemistry, 2013, # 35, p. 7952 - 7959]

16
[ 932741-19-0 ]
[ 55750-48-6 ]
N-[2-(2-(2-(2-Propynyloxy)ethoxy)ethoxy)ethyl]maleimide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: 2-(2-(2-(prop-2-yn-1-yloxy)ethoxy)ethoxy)ethanamine With sodium hydrogencarbonate In water at 0℃; for 0.25h; Stage #2: N-methoxycarbonylmaleimide In water at 0℃; for 3h;

Reference： [1]Cheng, Shuihong; Chang, Xuesong; Wang, Yan; Gao, George F.; Shao, Yiming; Ma, Liying; Li, Xuebing [Journal of Medicinal Chemistry, 2015, vol. 58, # 3, p. 1372 - 1379]

17
[ 55750-48-6 ]
[ 127828-22-2 ]
[ 131274-15-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium carbonate; at 0℃; for 2h;	(1) 20 g of tert-butyl terminal amino-terminated diethylene glycol carbamate was added to 100 ml of saturated sodium bicarbonate, 13.8 g of N-methoxycarbonyl maleimide was weighed and added slowly at 0C. The above solution was stirred for 2 h. TLC showed the reaction was complete and ethyl acetate was extracted 3 times. The ethyl acetate phase was dried over anhydrous sodium sulfate, spin-dried, and purified by column to obtain 22 g of a product. Yield: 90%
	With sodium hydrogencarbonate; In water; at 0℃; for 1.5h;	Step 1t-Butyl (2-(2-aminoethoxy)ethyl)carbamate (204 mg, 1 mmol) was dissolved in saturated aq. NaHCO3 (1 0 mL). The solution was cooled to 0 C. Methyl-2,5-dioxo-2,5- dihydro-1 H-pyrrole-1 -carboxylate (155 mg, 1.0 mmol) was then added. The reaction was stirred for 1 .5 h at 0 C. The pH was adjusted to 1 -2 with 2M HCl, and the mixture was extracted with EtOAc (3 X 20 mL). The combined organic phases was washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by ISCO using a 0-4% gradient of MeOH in DCM to obtain tert-butyl (2-(2-(2,5-dioxo-2,5-dihydro-1 H-pyrrol- 1 -yl)ethoxy)ethyl)carbamate. 1H NMR (400 MHz, CD3OD): 6.82 (s, 2H), 3.68 (t, J = 5.4 Hz, 2H), 3.59 (t, J = 5.4 Hz, 2H), 3.46 (t, J = 5.6 Hz, 2H), 3.1 8-3.14 (m, 2H), 1.43 (s, 9H). MS m/z 1 85.1 (M+1 -Boc). Retention time 0.918 min.

Reference： [1]Patent: CN107501378,2017,A .Location in patent: Paragraph 0038; 0042; 0046; 0050
[2]Patent: WO2015/189791,2015,A1 .Location in patent: Page/Page column 77

18
[ 55750-48-6 ]
[ 74536-29-1 ]
(S)-3-((tert-butoxycarbonyl)amino)-2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35.9%	With sodium hydrogencarbonate; at 5℃;	Compound 10 (CAS Reg. No. 73259-81-1, available from Chem-Impex, 50.0 mg, 0.245 mmol) was dissolved in 2 mL saturated sodium bicarbonate solution at RT. Compound 9 (CAS Reg. No. 55750-48-6, available from Sigma-Aldridge, 38.0 mg, 0.245 mmol) was added at 5 C. It took about 10 min for the suspension to become homogeneous and the reaction vessel was left in a freezer overnight. The mixture was acidified with 10% TFA and purified by preparative chromatography to give compound 7 (25.0 mg, 0.088 mmol, 35.9% yield) as a mixture of rotamers. MS: (+) m/z, 284.9 (M+l). For the major rotamer: NMR (400 MHz, METHANOL-di) delta ppm 1.38 (s, 9 H), 3.56 - 3.66 (m, 1 H), 3.69 - 3.80 (m, 1 H), 4.80 (dd, (0142) J=10.4, 4.3 Hz, 1 H), 6.87 (s, 2 H). Preparative chromatography conditions: Column: XBridge BEH Shield RP18 OBD Prep Column, 13thetaAlpha, 5 muiotaeta, 30 mm X 150 mm, 1/pkg [186002990], flow rate: 40 mL /min, 23 min gradient: 5-50%, acetonitrile (with 0.1% TFA)/ water (with 0.1% TFA). Fractions were collected at 20% acetonitrile in water.
30%	With sodium hydrogencarbonate; In water; at 0 - 20℃; for 2h;	To a solution of H-Dap (Boc) -OH (1.00 g, 4.9 mmol) in saturated NaHCO3(20 mL) at 0 was added compound 409 (2.30 g, 14.7 mmol) . The reaction was stirred at 0 for 1h, then warmed to r.t. and stirred for another hour. Then 1N KHSO4was added to adjust pH to 6 and the resulting mixture was extracted with EtOAc (2 × 50mL) . Combined organic layers were dried over Na2SO4, filtered, and concentrated to give compound 519 (0.42 g, 30%yield) . ESI m/z calcd for C12H15N2O6[M-H]-: 283.10, found 283.10.

Reference： [1]Patent: WO2017/196598,2017,A1 .Location in patent: Paragraph 0066; 0067
[2]Patent: WO2019/127607,2019,A1 .Location in patent: Page/Page column 12; 208
[3]Patent: WO2020/73345,2020,A1 .Location in patent: Page/Page column 180

19
[ 55750-48-6 ]
[ 101187-40-0 ]
tert-butyl (2-(2-(2-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethoxy)ethoxy)ethoxy)ethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium carbonate; at 0℃; for 2h;	(1) 20 g of tert-butyl terpolymer of terminal aminotrimesethylene glycol carbamate was added to 100 ml of saturated sodium bicarbonate, and 9.6 g of N-methoxycarbonylmaleimide was weighed out and added slowly at 0C. The above solution was stirred for 2 h.TLC showed the reaction was complete and ethyl acetate was extracted 3 times. The ethyl acetate phase was dried over anhydrous sodium sulfate, spin-dried, and purified by column to obtain 23 g of a product, yield: 90%.

Reference： [1]Patent: CN107501378,2017,A .Location in patent: Paragraph 0054

20
[ 55750-48-6 ]
[ 189209-27-6 ]
C₂₁H₃₆N₂O₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium carbonate; at 0℃; for 2h;	(1) Add 20 g of tert-butyl terminal aminopentahexaethylene glycol carbamate to 100 ml of saturated sodium bicarbonate, and weigh out 6.3 g of N-methoxycarbonylmaleimide, slowly adding it at 0C. The above solution was stirred for 2 h.TLC showed the reaction was complete and ethyl acetate was extracted 3 times. The ethyl acetate phase was dried over anhydrous sodium sulfate, spin-dried and purified by column to give 16.8 g of product, yield: 90%.

Reference： [1]Patent: CN107501378,2017,A .Location in patent: Paragraph 0058

21
[ 206265-98-7 ]
[ 55750-48-6 ]
C₂₅H₄₄N₂O₁₁ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium carbonate; at 0℃; for 2h;	(1) 20 g of tert-butyl end-capsule hexaglycidyl carbamate was added to 100 ml of saturated sodium bicarbonate, and 6.6 g of N-methoxycarbonylmaleimide was weighed out and slowly added at 0C. The above solution was stirred for 2 h.TLC showed the reaction was complete and ethyl acetate was extracted 3 times. The ethyl acetate phase was dried over anhydrous sodium sulfate, spin-dried and purified by column to give 19.4 g of product in 90% yield.

Reference： [1]Patent: CN107501378,2017,A .Location in patent: Paragraph 0062

22
[ 55750-48-6 ]
[ 890091-43-7 ]
C₂₉H₅₂N₂O₁₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium carbonate at 0℃; for 12h;	8.1 (1) 20 g of tert-butyl ether of terminal amino-terminated N-hexadecanethylene glycol carbamate is added to 100 ml of saturated sodium bicarbonate,5.0 g of N-methoxycarbonylmaleimide was weighed out and slowly added to the above solution at 0°C and stirred for 2 h. TLC showed the reaction was complete and ethyl acetate was extracted 3 times. The ethyl acetate phase was dried over anhydrous sodium sulfate, spin-dried and purified by column to give 19.5 g of product in a yield of 95%.

Reference： [1]Current Patent Assignee: HUNAN HUATENG PHARMACEUTICAL CO LTD - CN107501378, 2017, A Location in patent: Paragraph 0066

23
[ 55750-48-6 ]
[ 252881-74-6 ]
[ 518044-35-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate;	2.93 g (10.58 mmol) of <strong>[252881-74-6]tert-butyl 3-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}propanoate</strong> were dissolved in 100 ml of dioxane/water 1:1, and 3.28 g (21.15 mmol) of methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate and a saturated sodium bicarbonate solution were added until a pH of 6-7 had been reached. The solution was stirred at RT for 30 min and the 1,4-dioxane was then evaporated under reduced pressure. 200 ml of water were then added, and the mixture was extracted three times with in each case 300 ml of ethyl acetate. The organic extracts were combined, dried over magnesium sulphate and filtered. Concentration gave tert-butyl 3-(2-{2-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethoxy]ethoxy}ethoxy)propanoate as a brown oil which was then dried under high vacuum.

Reference： [1]Patent: US2018/169256,2018,A1

24
[ 55750-48-6 ]
[ 756525-95-8 ]
C₁₅H₂₃NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium hydrogencarbonate; In water; at 0 - 20℃; for 2h;	A mixture of compound 301 (8.16 g, 35.0 mmol, 1.0 eq. ) and saturated NaHCO3(40 mL) was cooled to 0 , to which compound 409 (5.43 g, 35.0 mmol, 1.0 eq. ) was added in portions. After stirring at 0 for 1 h, the reaction was warmed to r.t. and stirred for 1 h. The reaction was extracted with DCM (3 × 100 mL) and the organic extract was washed with brine, dried over anhydrous Na2SO4, concentrated and purified by SiO2column chromatography to give a white solid (6.76 g, 62%yield) . MS ESI m/z calcd for C15H23NO6[M+H]+314.15, found 314.15.

Reference： [1]Patent: WO2019/127607,2019,A1 .Location in patent: Page/Page column 12; 189-190

25
[ 55750-48-6 ]
[ 35146-32-8 ]
C₂₉H₂₃N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With sodium carbonate; In 1,4-dioxane; water; for 12h;Reflux; Inert atmosphere;	Compound 165 (1.0 g, 2.52 mmol) and N-methoxycarbonylmaleimide (429 mg, 2.77 mmol) were dissolved in 1,4-dioxane/distilled water (5 mL/2.5 mL), then sodium carbonate (267 mg, 2.52 mmol) was added thereto, and the mixture was heated under reflux for 12 hours under a nitrogen atmosphere. The reaction solution was concentrated under reduced pressure and dissolved in N,N-dimethylformamide (3 mL), then triethylamine (0.16 mL, 1.12 mmol) was added to the reaction solution, and the mixture was stirred for 10 hours under a nitrogen atmosphere. Distilled water (5 ml) was added to the reaction solution, then the reaction solution was acidified (pH 4) by addition of a 0.5 N aqueous hydrochloric acid solution and subjected to extraction using dichloromethane (3 × 10 mL), and then the extract was dried over anhydrous sodium sulfate. The resultant was filtered and concentrated under reduced pressure to obtain Compound 166 (504 mg, 32%). EI-MS m/z : [M+H]+ 478.4, [M+Na]+ 500.4.

Reference： [1]Patent: EP3604311,2020,A1 .Location in patent: Paragraph 0321; 0323

26
[ 55750-48-6 ]
[ 252881-74-6 ]
[ 518044-35-4 ]
[ 76-05-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate;	Trifluoroacetic acid/N-(2-aminoethyl)-3-(2-{2-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethoxy]ethoxy}ethoxy)propanamide (1:1) 2.93 g (10.58 mmol) of tert-Butyl 3-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}propanoate were dissolved in 100 ml of dioxane/water 1:1, and 3.28 g (21.15 mmol) of methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate and a saturated sodium bicarbonate solution were added until a pH of 6-7 had been reached. The solution was stirred at RT for 30 min and the 1,4-dioxane was then evaporated under reduced pressure. 200 ml of water were then added, and the mixture was extracted three times with in each case 300 ml of ethyl acetate. The organic extracts were combined, dried over magnesium sulphate and filtered. Concentration gave tert-Butyl 3-(2-{2-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethoxy]ethoxy}ethoxy)propanoate as a brown oil which was then dried under high vacuum.

Reference： [1]Patent: US2020/138970,2020,A1

27
[ 55750-48-6 ]
[ 127828-22-2 ]
[ 76-05-1 ]
[ 131274-17-4 ]

Yield	Reaction Conditions	Operation in experiment
70 mg	Stage #1: N-methoxycarbonylmaleimide; tert-butyl 2-(2-aminoethoxy)ethylcarbamate With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 120h; Stage #2: trifluoroacetic acid In dichloromethane at 20℃; for 0.25h;	Intermediate L12 Intermediate L12 Trifluoroacetic acid/1-[2-(2-aminoethoxy)ethyl]-1H-pyrrole-2,5-dione (1:1) 381 mg (2.46 mmol) of methyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate were added to 228 mg (1.12 mmol) of tert-Butyl [2-(2-aminoethoxy)ethyl]carbamate dissolved in 7 ml of dioxane/ water 1:1. 1.2 ml of a saturated sodium bicarbonate solution were then added and the reaction was stirred at RT. After a total of 5 days of stirring and 2 further additions of the same amounts of the sodium bicarbonate solution, the reaction was worked up by acidification with trifluoroacetic acid, concentration on a rotary evaporator and purification of the residue by preparative HPLC. The appropriate fractions were combined, the solvent was removed under reduced pressure and the residue was lyophilized from acetonitrile/water 1:1. The residue was taken up in 3 ml of dichloromethane, and 1 ml of trifluoroacetic acid was added. After 15 min of stirring at RT, the solvent was removed under reduced pressure and the residue was lyophilized from acetonitrile/water 1:1. This gave 70 mg (67% of theory over 2 steps) of the title compound as a resinous residue. [0774] HPLC (Method 11): Rt=0.2 min; [0775] LC-MS (Method 1): Rt=0.18 min; MS (ESIpos): m/z=185 (M+H)+.

Reference： [1]Current Patent Assignee: BAYER AG - US2020/138970, 2020, A1 Location in patent: Paragraph 0771-0775

28
[ 541-59-3 ]
[ 107-31-3 ]
[ 55750-48-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	With 4-methyl-morpholine In ethyl acetate at 0 - 20℃; for 1.5h;	108 Example 108. Synthesis of compound 409 At 0 °C, N-methylmorpholine (8.6mL, 78.5mmol) and methyl formate (6.0mL, 78.5mmol) were added to the maleimide (6.35g, 65.4mmol) in EtOAc (120mL) solution. The reaction was stirred at 0 °C for 30 minutes and at room temperature for 1 hour. The solid was filtered and the filtrate was concentrated. The residue was dissolved in dimethane and filtered through a silica gel column and eluted with dimethane to remove the color. The product was collected and concentrated, and the obtained solid was slurried with 10% ethyl acetate/petroleum ether to obtain 9.00 g of white solid (89% yield).

Reference： [1]Current Patent Assignee: HANGZHOU DAC BIOTECH CO LTD - TW2020/41237, 2020, A Location in patent: Paragraph 000422; 000423

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 55750-48-6 ]

Amides

[ 55750-49-7 ]

Ethyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate

Similarity: 0.91

[ 128372-89-4 ]

tert-Butyl 2-oxo-5,6-dihydropyridine-1(2H)-carboxylate

Similarity: 0.75

[ 128740-03-4 ]

Ethyl Allyl(2-oxoethyl)carbamate

Similarity: 0.69

[ 73286-70-1 ]

tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate

Similarity: 0.69

[ 930-88-1 ]

1-Methyl-1H-pyrrole-2,5-dione

Similarity: 0.67

Related Parent Nucleus of
[ 55750-48-6 ]

Aliphatic Heterocycles

[ 55750-49-7 ]

Ethyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate

Similarity: 0.91

[ 73286-70-1 ]

tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate

Similarity: 0.69

[ 930-88-1 ]

1-Methyl-1H-pyrrole-2,5-dione

Similarity: 0.67

[ 25021-08-3 ]

2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid

Similarity: 0.62

[ 4144-22-3 ]

1-(tert-Butyl)-1H-pyrrole-2,5-dione

Similarity: 0.62

Pyrrolines

[ 55750-49-7 ]

Ethyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate

Similarity: 0.91

[ 73286-70-1 ]

tert-Butyl 2,5-dihydro-1H-pyrrole-1-carboxylate

Similarity: 0.69

[ 930-88-1 ]

1-Methyl-1H-pyrrole-2,5-dione

Similarity: 0.67

[ 25021-08-3 ]

2-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid

Similarity: 0.62

[ 4144-22-3 ]

1-(tert-Butyl)-1H-pyrrole-2,5-dione

Similarity: 0.62

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 55750-48-6 ] {[proInfo.proName]}

Quality Control of [ 55750-48-6 ]

Related Doc. of [ 55750-48-6 ]

Product Details of [ 55750-48-6 ]

Calculated chemistry of [ 55750-48-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 55750-48-6 ]

Application In Synthesis of [ 55750-48-6 ]

[ 55750-48-6 ] Synthesis Path-Upstream 1~4

[ 55750-48-6 ] Synthesis Path-Downstream 1~28

Related Functional Groups of [ 55750-48-6 ]

Amides

Related Parent Nucleus of [ 55750-48-6 ]

Aliphatic Heterocycles

Pyrrolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 55750-48-6 ]

Related Parent Nucleus of
[ 55750-48-6 ]