[ CAS No. 59703-00-3 ] {[proInfo.proName]}

Name: 59703-00-3|4-Ethyl-2,3-dioxopiperazine-1-carbonyl chloride|95%
Brand: Ambeed
SKU: A795177
Rating: 90 (32 reviews)

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

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Limited Quantity	USD 15-60
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Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

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Quality Control of [ 59703-00-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 59703-00-3 ]

SDS Specification

Alternatived Products of [ 59703-00-3 ]

Product Details of [ 59703-00-3 ]

CAS No. :	59703-00-3	MDL No. :	MFCD00067054
Formula :	C₇H₉ClN₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SXVBQOZRZIUHKU-UHFFFAOYSA-N
M.W :	204.61	Pubchem ID :	108813
Synonyms :

Calculated chemistry of [ 59703-00-3 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.57
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	53.06
TPSA :	57.69 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) :	-7.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.84
Log Po/w (XLOGP3) :	0.6
Log Po/w (WLOGP) :	-0.73
Log Po/w (MLOGP) :	-0.39
Log Po/w (SILICOS-IT) :	0.13
Consensus Log Po/w :	0.09

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.35
Solubility :	9.04 mg/ml ; 0.0442 mol/l
Class :	Very soluble
Log S (Ali) :	-1.39
Solubility :	8.43 mg/ml ; 0.0412 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.8
Solubility :	32.3 mg/ml ; 0.158 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.94

Safety of [ 59703-00-3 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	1759
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 59703-00-3 ]

* 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 [ 59703-00-3 ]
Downstream synthetic route of [ 59703-00-3 ]

[ 59703-00-3 ] Synthesis Path-Upstream 1~2

1
[ 85208-10-2 ]
[ 59703-00-3 ]
[ 85208-19-1 ]
[ 59702-31-7 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 6, p. 1227 - 1236

2
[ 59703-00-3 ]
[ 62893-19-0 ]

Yield	Reaction Conditions	Operation in experiment
42%	With potassium carbonate In water; ethyl acetate at 20℃;	D -7-(4-Hydroxyphenylacetamido)-3-(1-methyl-1H-tetrazol-5-yl)thiomethylcephem-4-carboxylic acid (500 mg) was suspended at room temperature in water (10 mL). After addition of potassium carbonate (230 mg, 1.5 equiv.) the suspension became a clear solution. To this mixture, ethyl acetate (5 mL) and ethyl-2,3-dioxo-1-piperazinecarbonylchloride (210 mg, 1 equiv.) were added. After stirring overnight, the reaction was analyzed by analytical HPLC showing 42percent of the desired product cefoperazone based on the starting material.

Reference： [1] Patent: US2015/112057, 2015, A1, . Location in patent: Paragraph 0063

[ 59703-00-3 ] Synthesis Path-Downstream 1~66

1
[ 88585-78-8 ]
[ 59703-00-3 ]
(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(4-ethyl-2,3-dioxo-piperazine-1-carbonyloxymethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester [ No CAS ]

Reference： [1]Heterocycles,1990,vol. 30,p. 799 - 812

2
[ 72699-69-5 ]
[ 59703-00-3 ]
[ 85208-16-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; sodium hydroxide; In tetrahydrofuran; methanol; water; at 0 - 10℃; for 1.5h;	To a solution of the above amino acid (2.06 g, 6 mmol) in THF (60 mL) and water (60 mL) was added a solution of NaOH (480 mg, 12 mmol) in water (5 mL) at 0oC, followed by aqueous saturated NaHCO3 (20 mL), a solution of <strong>[59703-00-3]4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride</strong> (1.54 g, 7.5 mmol) in THF (8 mL), and MeOH (160 mL). The reaction mixture was stirred between 0 - 10 C for 1.5 h, then concentrated in vacuo, acidified with 1 N HCl to pH ~ 2, extracted with EtOAc. The organic extracts were combined, dried over Na2SO4, concentrated in vacuo to afford the crude product, 2.3 g, which was used directly for the next Step without further purification. ESI-MS m/z 476 (M+1)+.

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 1227 - 1236
[2]Patent: WO2021/108023,2021,A1 .Location in patent: Paragraph 00268

3
[ 85208-10-2 ]
[ 59703-00-3 ]
[ 85208-19-1 ]
[ 59702-31-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 1227 - 1236

4
[ 73910-42-6 ]
[ 59703-00-3 ]
[ 73910-43-7 ]

Reference： [1]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 1563 - 1577

5
[ 73910-33-5 ]
[ 59703-00-3 ]
[ 73910-34-6 ]

Reference： [1]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 1563 - 1577

6
7β-<(2R)-2-phenyl-2-amino>acetylamino-1-carba-1-dethia-3-cephem-4-carboxylic acid [ No CAS ]
[ 59703-00-3 ]
7β-<(2R)-2-phenyl-2-(4-ethyl-2,3-dioxopiperazine-1-yl-carbonyl)amino>acetylamino-1-carba-1-dethia-3-cephem-4-carboxylic acid [ No CAS ]

Reference： [1]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 1563 - 1577

7
[ 161855-50-1 ]
[ 59703-00-3 ]
(4R,5S,6S)-3-((2R,3R)-2-[(4-Ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-methyl}-tetrahydro-furan-3-ylsulfanyl)-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 3063 - 3068

8
(4R,5S,6S)-3-(5-Aminomethyl-tetrahydro-furan-3-ylsulfanyl)-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid [ No CAS ]
[ 59703-00-3 ]
Sodium; (4R,5S,6S)-3-(5-[(4-ethyl-2,3-dioxo-piperazine-1-carbonyl)-amino]-methyl}-tetrahydro-furan-3-ylsulfanyl)-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 3063 - 3068

Yield	Reaction Conditions	Operation in experiment
		In the same manner as above, a sodium salt of 6-[D(-)-α-(4-ethyl-2,3-dioxo-1-piperazinocarbonylamino)-p-hydroxyphenylacetamido]penicillanic acid, m.p. 175 C (decomp.), yield 72 %, was obtained from 4-ethyl-2,3-dioxo-1-piperazinocarbonyl chloride and a triethylamine salt of 6-[D(-)-α-amino-p-hydroxyphenylacetamido]penicillanic acid.
		In the same manner as above, a sodium salt of 6-[D(-)-α-(4-ethyl-2,3-dioxo-1-piperazinocarbonylamino)-p-hydroxyphenylacetamido]penicillanic acid, m.p. 175 C. (decomp.), yield 72%, was obtained from 4-ethyl-2,3-dioxo-1-piperazinocarbonyl chloride and a triethylamine salt of 6-[D(-)-α-amino-p-hydroxyphenylacetamido]penicillanic acid.

10
α-amino(3,4-dihydroxyphenyl)acetic acid hydrobromide [ No CAS ]
[ 59703-00-3 ]
[ 74985-17-4 ]