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[ CAS No. 672883-23-7 ] {[proInfo.proName]}

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2D 3D

Chemical Structure| 672883-23-7

Chemical Structure| 672883-23-7

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Quality Control of [ 672883-23-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 672883-23-7 ]

SDS Specification

Alternatived Products of [ 672883-23-7 ]

Product Details of [ 672883-23-7 ]

CAS No. :	672883-23-7	MDL No. :	MFCD20257110
Formula :	C₉H₁₆N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PFHVTCWJHBHEFA-LURJTMIESA-N
M.W :	200.24	Pubchem ID :	45091936
Synonyms :

Calculated chemistry of [ 672883-23-7 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.78
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	54.69
TPSA :	67.43 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) :	-7.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.95
Log Po/w (XLOGP3) :	0.02
Log Po/w (WLOGP) :	0.02
Log Po/w (MLOGP) :	0.03
Log Po/w (SILICOS-IT) :	0.27
Consensus Log Po/w :	0.46

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.83
Solubility :	29.6 mg/ml ; 0.148 mol/l
Class :	Very soluble
Log S (Ali) :	-0.99
Solubility :	20.6 mg/ml ; 0.103 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.66
Solubility :	4.42 mg/ml ; 0.0221 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.66

Safety of [ 672883-23-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 672883-23-7 ]

* 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 [ 672883-23-7 ]
Downstream synthetic route of [ 672883-23-7 ]

[ 672883-23-7 ] Synthesis Path-Upstream 1~2

1
[ 330680-82-5 ]
[ 672883-23-7 ]

Reference： [1] Patent: WO2004/22536, 2004, A1, . Location in patent: Page 45-46

2
[ 672883-23-7 ]
[ 672883-63-5 ]

Reference： [1] Patent: WO2004/22536, 2004, A1, . Location in patent: Page 74

[ 672883-23-7 ] Synthesis Path-Downstream 1~6

1
[ 330680-82-5 ]
[ 672883-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium 10% on activated carbon; In methanol; under 2068.65 Torr; for 1h;	Step 3: To a solution of azido ester (600 mg, 2.323 mmol) in methanol (20 ml) was added 10 percent Pd/C (20 mg) and the mixture was agitated under 40 psi hydrogen gas pressure for 1 h in Paar hydrogenation apparatus. The reaction mixture was filtered through a celite bed and the filtrate was evaporated under reduced pressure to give the crude product. The crude product was purified by chromatography on silica gel using 10 percent methanol in chloroform to give 200 mg 5 of the product as white solid, mp 164-167 °C; IR (KBr) 3327, 2980, 1685, 1543, 1276, 1 170 cm-1; 1H NMR (300 MHz, CDC13) delta 1.44 (s, 9 H), 2.19 (dd, J = 17.1, 5.2 Hz, 1 H), 2.68 (dd, J = 17.1, 8.1 Hz, 1 H), 3.24 (dd, J= 9.9, 4.2 Hz, 1 H), 3.70 (dd, J= 9.9, 6.3 Hz, 1 H), 4.36-4.42 (m, 1 H), 4.86 (brs, 1 H), 5.90 (brs, 1 H).

Reference： [1]Patent: WO2004/22536,2004,A1 .Location in patent: Page 45-46

2
[ 672883-23-7 ]
[ 672883-63-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethyl acetate; at 20.0℃; for 4h;	Example -31; (3S)-3-(3-Cyclopentyloxy-4-methoxyphenylcarboxamido)-5-oxoazolane. Step 1: (3S)-3-Amino-5-oxoazolane hydrochloride was prepared by deprotection of (3S)-3-(N-BOC-Amino)-5-oxoazolane (60 mg, 0.299 mmol) using 15 percent HC1 in ethyl acetate (5 ml) at RT for 4 h.

Reference： [1]Patent: WO2004/22536,2004,A1 .Location in patent: Page 74

3
[ 672883-23-7 ]
[(3S)-5-oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-yl]carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Patent: EP2674430,2013,A1

4
[ 672883-23-7 ]
[ 443956-09-0 ]
[(6-{(4S)-4-[(tert-butoxycarbonyl)amino]-2-oxopyrrolidin-1-yl}-2-nitropyridin-3-yl)oxy]acetic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With potassium phosphate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 100.0℃; for 6h;Inert atmosphere;	A mixture of <strong>[672883-23-7][(3S)-5-oxopyrrolidin-3-yl]carbamic acid tert-butyl ester</strong> (synthesized with reference to WO2004/22536; 505 mg, 2.52 mmol), [(6-bromo-2-nitropyridin-3-yl)oxy]acetic acid ethyl ester (synthesized with reference to WO2004/2992; 769 mg, 2.52 mmol), palladium acetate (56.6 mg, 0.252 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (157 mg, 0.252 mmol), potassium phosphate (1.74 g, 7.56 mmol) and 1,4-dioxane (25 ml) was stirred under a stream of nitrogen gas at 100°C for 6 hours. After cooling, ethyl acetate was added to the reaction solution to remove the insoluble material by filtration. The obtained filtrate was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 380 mg (36percent) of the title compound in the form of a light brown syrup. 1H-NMR(400MHz,CDCl3)delta:1.25-1.33(3H,m),1.45(9H,s),2.61(1H,dd,J=17.8,4.6Hz),3.02(1H,dd,J=17.8,8.0Hz),3.93-3.99(1H,m),4.24-4.32(3H,m),4.40(1H,s),4.76(2H,s),4.77-4.88(1 H,m),7.52(1 H,d,J=9.2Hz),8.61 (1 H,d,J=9.2Hz). MS(ESI)m/z:425(M+H)+.

Reference： [1]Patent: EP2674430,2013,A1 .Location in patent: Paragraph 0110

5
[ 672883-23-7 ]
[ 179897-89-3 ]
tert-butyl N-[(3S)-1-(4-bromo-2-cyanophenyl)-5-oxopyrrolidin-3-yl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.5 g		Step 1 tert-Butyl N-[(3S)-1-(4-bromo-2-cyanophenyl)-5-oxopyrrolidin-3-yl]carbamate To a solution of <strong>[672883-23-7]tert-butyl ((S)-5-oxopyrrolidin-3-yl)carbamate</strong> (2.0 g) in N,N-dimethylformamide (50 ml), sodium hydride (55percent oil, 0.65 g) was added under ice cooling, and the mixture was stirred at the same temperature as above for 10 minutes. 5-Bromo-2-fluorobenzonitrile (3.0 g) was added to the reaction solution, and the mixture was stirred at room temperature for 1 hour. Ice water and a saturated aqueous solution of ammonium chloride were added to the reaction solution, followed by extraction with ethyl acetate. The extract was washed with water and saturated saline in this order and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain the title compound (1.5 g). 1H-NMR (CDCl3) delta: 1.46 (9H, s), 2.52 (1H, dd, J=17.5, 4.8 Hz), 2.96 (1H, dd, J=17.5, 7.9 Hz), 3.81 (1H, d, J=6.7 Hz), 4.19 (1H, dd, J=10.0, 6.3 Hz), 4.49 (1H, br s), 4.98 (1H, br s), 7.32 (1H, d, J=8.5 Hz), 7.76 (1H, dd, J=8.8, 2.1 Hz), 7.83 (1H, d, J=2.4 Hz).
1.5 g		To a solution of <strong>[672883-23-7]tert-butyl ((S)-5-oxopyrrolidin-3-yl)carbamate</strong> (2.0 g) in N,N-dimethylformamide (50 ml), sodium hydride (55percent oil, 0.65 g) was added under ice cooling, and the mixture was stirred at the same temperature as above for 10 minutes. 5-Bromo-2-fluorobenzonitrile (3.0 g) was added to the reaction solution, and the mixture was stirred at room temperature for 1 hour. Ice water and a saturated aqueous solution of ammonium chloride were added to the reaction solution, followed by extraction with ethyl acetate. The extract was washed with water and saturated saline in this order and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain the title compound (1.5 g). (0462) 1H-NMR (CDCl3) delta: 1.46 (9H, s), 2.52 (1H, dd, J=17.5, 4.8 Hz), 2.96 (1H, dd, J=17.5, 7.9 Hz), 3.81 (1H, d, J=6.7 Hz), 4.19 (1H, dd, J=10.0, 6.3 Hz), 4.49 (1H, br s), 4.98 (1H, br s), 7.32 (1H, d, J=8.5 Hz), 7.76 (1H, dd, J=8.8, 2.1 Hz), 7.83 (1H, d, J=2.4 Hz).

Reference： [1]Patent: US2015/51190,2015,A1 .Location in patent: Paragraph 0405-0407
[2]Patent: US2016/46639,2016,A1 .Location in patent: Paragraph 0461; 0462

6
[ 672883-23-7 ]
[ 202865-85-8 ]
tert-butyl N-[(3S)-1-(4-bromo-3-methylphenyl)-5-oxopyrrolidin-3-yl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.8 g	With copper(l) iodide; N,N-dimethylethylenediamine; cesium fluoride; In acetonitrile; at 100.0℃; for 3h;Inert atmosphere;	Step 1 tert-Butyl N-[(3S)-1-(4-bromo-3-methylphenyl)-5-oxopyrrolidin-3-yl]carbamate A suspension of <strong>[202865-85-8]2-bromo-5-iodotoluene</strong> (1.5 g), tert-butyl ((S)-5-oxopyrrolidin-3-yl)carbamate (2.7 g), copper iodide (95 mg), cesium fluoride (1.9 g), and N,N-dimethylethylenediamine (0.11 ml) in acetonitrile (20 ml) was stirred at 100° C. for 3 hours under a nitrogen atmosphere. After cooling, a saturated aqueous solution of ammonium chloride was added to the reaction solution, followed by extraction with ethyl acetate. The extract was washed with a 10percent aqueous sodium thiosulfate solution and saturated saline in this order and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform-methanol) to obtain the title compound (1.8 g). 1H-NMR (CDCl3) delta: 1.45 (9H, s), 2.40 (3H, s), 2.47 (1H, dd, J=17.2, 4.5 Hz), 2.96 (1H, dd, J=17.2, 8.2 Hz), 3.69 (1H, d, J=9.7 Hz), 4.13 (1H, dd, J=9.7, 6.7 Hz), 4.41 (1H, br s), 4.83 (1H, br s), 7.29 (1H, d, J=8.5 Hz), 7.47-7.52 (2H, m).
1.8 g	With copper(l) iodide; N,N-dimethylethylenediamine; cesium fluoride; In acetonitrile; at 100.0℃; for 3h;Inert atmosphere;	A suspension of <strong>[202865-85-8]2-bromo-5-iodotoluene</strong> (1.5 g), tert-butyl ((S)-5-oxopyrrolidin-3-yl)carbamate (2.7 g), copper iodide (95 mg), cesium fluoride (1.9 g), and N,N-dimethylethylenediamine (0.11 ml) in acetonitrile (20 ml) was stirred at 100° C. for 3 hours under a nitrogen atmosphere. After cooling, a saturated aqueous solution of ammonium chloride was added to the reaction solution, followed by extraction with ethyl acetate. The extract was washed with a 10percent aqueous sodium thiosulfate solution and saturated saline in this order and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform-methanol) to obtain the title compound (1.8 g). (0440) 1H-NMR (CDCl3) delta: 1.45 (9H, s), 2.40 (3H, s), 2.47 (1H, dd, J=17.2, 4.5 Hz), 2.96 (1H, dd, J=17.2, 8.2 Hz), 3.69 (1H, d, J=9.7 Hz), 4.13 (1H, dd, J=9.7, 6.7 Hz), 4.41 (1H, br s), 4.83 (1H, br s), 7.29 (1H, d, J=8.5 Hz), 7.47-7.52 (2H, m).

Reference： [1]Patent: US2015/51190,2015,A1 .Location in patent: Paragraph 0383-0385
[2]Patent: US2016/46639,2016,A1 .Location in patent: Paragraph 0439; 0440

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Ghs Precautionary Statements

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.
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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.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
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P285	In case of inadequate ventilation wear respiratory protection.
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Code	Phrase
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P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
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P378
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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.
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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
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P401
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P411
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Ghs Hazard Statements

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
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H225	Highly flammable liquid and vapour
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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