[ CAS No. 55750-49-7 ]

Name: Ethyl 2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate
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Product Details of [ 55750-49-7 ]

CAS No. :	55750-49-7	MDL No. :	MFCD16619570
Formula :	C₇H₇NO₄	Boiling Point :	257.3±23.0°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	XUXSQROIUORWRI-UHFFFAOYSA-N
M.W :	169.14	Pubchem ID :	319934
Synonyms :

Computed Properties of [ 55750-49-7 ]

TPSA :Topological Polar Surface Area	63.7	H-Bond Acceptor Count :	4
XLogP3 :	0	H-Bond Donor Count :	0
SP3 :	0.29	Rotatable Bond Count :	2

Safety of [ 55750-49-7 ]

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 [ 55750-49-7 ]

Upstream synthesis route of [ 55750-49-7 ]
Downstream synthetic route of [ 55750-49-7 ]

[ 55750-49-7 ] Synthesis Path-Upstream 1~1

1
[ 541-59-3 ]
[ 541-41-3 ]
[ 55750-49-7 ]

Yield	Reaction Conditions	Operation in experiment
50%	With 4-methyl-morpholine In water; ethyl acetate	1) Ethyl-2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate 9.7 g (0.1 mol) of maleimide are solubilized in 50 ml of ethyl acetate and 1.1 ml of N-methylmorpholine at 5° C. 1.1 ml of ethyl chloroformate are added dropwise. The mixture is stirred for 1/2 hour. The insoluble material is removed by filtration. The filtrate is washed with 50 ml of water. The organic phase is dried over MgSO₄ and is then concentrated under vacuum. The oil obtained is purified on Merck Geduran.(R). silica gel (40-63 μm). Elution: CH₂Cl₂/ACOEt 66/34. 16.9 g are isolated with a yield of 50percent. Mass spectrum: M/z=170.1 (ES+) theoretical M=169
41%	With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 4.00 h;	Ethyl chloroformate (0.38 ml, 4 mmol) was added dropwise to a stirred solution maleimide (0.3 g, 3 mmol) and triethylamine (0.5 ml, 3.5 mmol) in dimethylformamide (2 ml) at 0-5° C. The reaction mixture was allowed to warm to room temperature and stand for 4 h. Methyl alcohol (1 ml) was added, diluted with chloroform (20 ml) and washed with water (3*10 ml). The chloroform solution was dried (Na₂SO₄) and concentrated in vacuum. The residue was purified in chloroform and hexane on a silica gel column to give N-ethoxycarbonyl-maleimide (yield 41percent). ¹H NMR (CDCl₃) δ 1.34 (3H, t, CH₃), 4.27 (2H, q, CH₂), 6.21 (1H, d, CH=), 6.72 (1H, d, CH=).

Reference： [1] Organic Letters, 2015, vol. 17, # 23, p. 5846 - 5849
[2] Chemical Communications, 2014, vol. 50, # 7, p. 859 - 861
[3] Patent: US2010/297025, 2010, A1
[4] Patent: US9273304, 2016, B2. Location in patent: Page/Page column 16

[ 55750-49-7 ] Synthesis Path-Downstream 1~10

1
[ 55750-49-7 ]
[ 106788-30-1 ]

Reference： [1]Helvetica chimica acta,1975,vol. 58,p. 531 - 541

4
[ 55750-49-7 ]
2-((5,5-dimethyl-1,3,2-dioxaborinan-2-yl)methyl)-N-phenylacrylamide [ No CAS ]
C₁₇H₁₈N₂O₅ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 6096 - 6098

5
[ 55750-49-7 ]
2-((5,5-dimethyl-1,3,2-dioxaborinan-2-yl)methyl)-N-phenylacrylamide [ No CAS ]
8-methylene-6-phenyl-1-oxa-6-azaspiro[4.4]non-3-ene-2,7-dione [ No CAS ]
C₁₇H₁₈N₂O₅ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 6096 - 6098

6
[ 55750-49-7 ]
2-((5,5-dimethyl-1,3,2-dioxaborinan-2-yl)methyl)-N-phenylacrylamide [ No CAS ]
8-methylene-6-phenyl-1-oxa-6-azaspiro[4.4]non-3-ene-2,7-dione [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 6096 - 6098

7
[ 55750-49-7 ]
(S)-5’-fluorenylmethyloxycarbonylamino-1’-(3”-methyl-1”,2”,4”-oxadiazoi-5”-yl)-1’-tert-butoxycarbonylaminopentane [ No CAS ]
(S)-5’-(N-maleimido)-1’-(3”-methyl-1”,2”,4”-oxadiazol-5”-yl)-1’-tert-butoxycarbonylaminopentane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%		A solution of 82 (278 mg, 0.55 minol) in Tesser?s Base (20 mL, i,4-dioxane/methanol/4M NaOH, 30:9:1 v/v) was stirred at room temperature for 10 minutes. The solution was then concentrated in vacuo to afford a yellow oil, which was used without further purification. To the crude oil was added a mixture of 45 (163 mg, 0.66 minol) in saturated aqueous sodium bicarbonate (14 mL), and the mixture stirred at room temperature for 5 minutes. Themixture was then extracted with dichloromethane (3 x), the combined organic layers dried over anhydrous magnesium sulfate, filtered and the solution concentrated in vacuo. Purification by column chromatography (EtOAc/hexanes, 1:2) afforded the title compound 83 (100 mg, 50%) as a yellow oil. [aID232 = -1.0 (c 1.00 in CHCI3); 1H NMR (400 MHz, CDCI3) oe 1.33-1.41 (2H, m, H-3?), 1.44 (9H, s, Boc), 1.59-1.69 (2H, m, H-4?), 1.81-1.95(2H, m, H-2?), 2.39 (3H, s, 3?-Me), 3.51 (2H, t, J = 7.2 Hz, H-5?), 4.97-5.01 (iH, m, H-i?),5.09 (iH, d, J = 7.4 Hz, NH), 6.69 (2H, 5, H-3, H-4); 13C NMR (100 MHz, CDCI3) oe 11.5 (CH3, 3?-Me), 22.4 (CH2, C-3?), 27.9 (CH2, C-4?), 28.3 (3 x CH3, Boc), 33.4 (CH2, C-2?),37.2 (CH2, C-5?), 48.0 (CH, C-i?), 80.4 (C, Boc), 134.1 (2 x CH, C-3, C-4), i55.0 (C, Boc),i67.i (C, C-3?), i70.8 (2 x C, C-2, C-5), 179.1 (C, C-5?); Vmax (cm1) 3336, 2925, i702,1514, i367, ii64, 828; HRMS-ESI [M+Na] Calcd. for C17H24N4O5Na 387.i639, found387. i652.

Reference： [1]Patent: WO2017/95237,2017,A1.Location in patent: Page/Page column 56; 150; 151

8
[ 55750-49-7 ]
[ 73548-77-3 ]
methyl (S)-6’-(N-maleimido)-2’-tert-butoxycarbonylaminohexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 62 (2.12 g, 5.4 minol), acetic acid (1.5 mL) and palladium-on-carbon (0.2 g,10% w/w) in methanol (30 mL) was stirred at room temperature under a hydrogenatmosphere for 90 minutes. The mixture was then filtered through Celite and the solution concentrated in vacuo to afford a yellow oil, which was used without further purification. To the crude oil was added a mixture of 45 (1.36 g, 8.1 minol) in saturated aqueous sodium bicarbonate (50 mL) at 0 C, and the mixture stirred at 0 C for 10 minutes. Acetonitrile (25mL) was then added and the mixture stirred at room temperature for 90 min. The mixture was then extracted with dichloromethane (3 x), the combined organic layers dried over anhydrous magnesium sulfate, filtered and the solution concentrated in vacuo. Purification by column chromatography (EtOAc/hexanes, 1:2) afforded the title compound 63 (1.43 g, 78%) as a yellow oil. [aID237 = + 11.1 (c 1.00 in CHCI3); 1H NMR (400 MHz, CDCI3) oe 1.31-1.38 (2H, m, H-4?), 1.44 (9H, s, Boc), 1.59-1.67 (3H, m, Hb-3?, H-5?), 1.79-1.83 (1H, m,Ha3?), 3.51 (2H, t, J = 7.2 Hz, H-6?), 3.74 (3H, s, OMe), 4.27 (1H, m, H-2?), 5.08 (1H, d, J= 7.9 Hz, NH), 6.70 (2H, s, H-3, H-4); 13C NMR (100 MHz, CDCI3) oe 22.4 (CH2, C-4?), 28.0(CH2, C-5?), 28.3 (3 x CH3, Boc), 32.1 (CH2, C-3?), 37.3 (CH, C-6?), 52.2 (CH3, OMe), 53.2(CH, C-2?), 79.8 (C, Boc), 134.1 (2 x CH, C-3, C-4), 155.3 (C, Boc), 170.7 (2 x C, C-2, C-5), 173.1 (C, C-i?); vmax (cm1) 3374, 2952, 1698, 1365, 1160, 828, 694; HRMS-ESI[M+Na] Calcd. for C16H24N2O6Na 363.1527, found 363.1528.

Reference： [1]Patent: WO2017/95237,2017,A1.Location in patent: Page/Page column 56; 125; 126

9
[ 55750-49-7 ]
C₁₁H₁₃Br₂NO₄ [ No CAS ]

Reference： [1]Patent: WO2017/95237,2017,A1

10
[ 55750-49-7 ]
tert-butyl 3-(3-bromo-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethylcarbamate [ No CAS ]

Reference： [1]Patent: WO2017/95237,2017,A1

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H316	Causes mild skin irritation
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H319	Causes serious eye irritation
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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. 55750-49-7 ]

Quality Control of [ 55750-49-7 ]

Related Doc. of [ 55750-49-7 ]

Product Details of [ 55750-49-7 ]

Computed Properties of [ 55750-49-7 ]

Safety of [ 55750-49-7 ]

Application In Synthesis of [ 55750-49-7 ]

[ 55750-49-7 ] Synthesis Path-Upstream 1~1

[ 55750-49-7 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 55750-49-7 ]

Amides

Related Parent Nucleus of [ 55750-49-7 ]

Aliphatic Heterocycles

Pyrrolines

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Physical hazards

Health hazards

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[ 55750-49-7 ]