[ CAS No. 34622-39-4 ] {[proInfo.proName]}

Name: 34622-39-4|(S)-2-Piperidinone-6-carboxylic acid|97%
Brand: Ambeed
SKU: A540277
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3d Animation Molecule Structure of 34622-39-4

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Quality Control of [ 34622-39-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 34622-39-4 ]

SDS Specification

Alternatived Products of [ 34622-39-4 ]

Product Details of [ 34622-39-4 ]

CAS No. :	34622-39-4	MDL No. :	MFCD03839863
Formula :	C₆H₉NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FZXCPFJMYOQZCA-BYPYZUCNSA-N
M.W :	143.14	Pubchem ID :	11126383
Synonyms :

Calculated chemistry of [ 34622-39-4 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	37.53
TPSA :	66.4 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) :	-7.46 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.66
Log Po/w (XLOGP3) :	-0.41
Log Po/w (WLOGP) :	-0.64
Log Po/w (MLOGP) :	-0.55
Log Po/w (SILICOS-IT) :	0.15
Consensus Log Po/w :	-0.16

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-0.4
Solubility :	56.6 mg/ml ; 0.395 mol/l
Class :	Very soluble
Log S (Ali) :	-0.52
Solubility :	43.2 mg/ml ; 0.302 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.33
Solubility :	67.4 mg/ml ; 0.471 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.71

Safety of [ 34622-39-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 34622-39-4 ]

* 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 [ 34622-39-4 ]
Downstream synthetic route of [ 34622-39-4 ]

[ 34622-39-4 ] Synthesis Path-Upstream 1~11

1
[ 1118-90-7 ]
[ 34622-39-4 ]

Yield	Reaction Conditions	Operation in experiment
45%	for 3 h; Inert atmosphere; Reflux	(a) (S)-6-Oxo-piperidine-2-carboxylic acid A mixture of (S)-2-amino-hexanedioic acid (50 g, 310.25 mmol), acetic acid (100 mL), and water (400 mL) water was refluxed for 3 h. The unchanged starting amino acid was filtered off (24 g) and the filtrate evaporated, dissolved in hot water (50 mL) and then cooled. A crystalline precipitate formed which was filtered to provide the title intermediate (20 g, 45percent yield).

Reference： [1] Chemical and Pharmaceutical Bulletin, 1999, vol. 47, # 11, p. 1525 - 1531
[2] Journal of the American Chemical Society, 1982, vol. 104, # 16, p. 4446 - 4450
[3] Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1654 - 1658
[4] Chemical Communications, 2010, vol. 46, # 9, p. 1413 - 1415
[5] Patent: US2013/287731, 2013, A1, . Location in patent: Paragraph 0295; 0296
[6] Patent: US2013/190249, 2013, A1, . Location in patent: Page/Page column
[7] Patent: US2015/31627, 2015, A1, . Location in patent: Page/Page column
[8] Patent: WO2013/107291, 2013, A1, . Location in patent: Page/Page column 92; 93
[9] Patent: WO2015/10626, 2015, A1, . Location in patent: Page/Page column 93
[10] Patent: WO2015/10297, 2015, A1, . Location in patent: Page/Page column 93

2
[ 2389-60-8 ]
[ 34622-39-4 ]

Reference： [1] Journal of the American Chemical Society, 1982, vol. 104, # 16, p. 4446 - 4450

3
[ 2418-95-3 ]
[ 34622-39-4 ]

Reference： [1] Journal of the American Chemical Society, 1982, vol. 104, # 16, p. 4446 - 4450

4
[ 6033-32-5 ]
[ 34622-39-4 ]

Reference： [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1654 - 1658

5
[ 24325-14-2 ]
[ 34622-39-4 ]

Reference： [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1654 - 1658

6
[ 102922-72-5 ]
[ 34622-39-4 ]

Reference： [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1654 - 1658

7
[ 82228-91-9 ]
[ 34622-39-4 ]

Reference： [1] Journal of the American Chemical Society, 1982, vol. 104, # 16, p. 4446 - 4450

8
[ 47307-39-1 ]
[ 34622-39-4 ]

Reference： [1] Journal of the American Chemical Society, 1982, vol. 104, # 16, p. 4446 - 4450

9
[ 82228-90-8 ]
[ 34622-39-4 ]

Reference： [1] Journal of the American Chemical Society, 1982, vol. 104, # 16, p. 4446 - 4450

10
[ 1155-64-2 ]
[ 34622-39-4 ]

Reference： [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1654 - 1658

11
[ 83793-27-5 ]
[ 34622-39-4 ]

Reference： [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1654 - 1658

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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:
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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.
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P372	Explosion risk in case of fire.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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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.
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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.
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	With acetic acid; at 110℃;	A solution of (S)-2-aminohexanedioic acid (470mg, 2.9 mmol) in 20percent AcOH (5 mL) was stirred at 110 °C overnight. The solvent was removed in vacuo and the residue was dissolved in EtOH (lOmL). The unreacted amino acid was precipitated and filtered off. The filtrate was concentrated to give the crude desired product which was used directly in the next step. MS: 142.1 (M-1).
	With acetic acid; at 110℃;	Step A. (S)-6-Oxopiperidine-2-carboxylic acid. A solution of (S)-2-aminohexanedioic acid (470 mg, 2.9 mmol) in 20percent AcOH (5 mL) was stirred at 1 10 °C overnight. The solvent was removed in vacuo and the residue was dissolved in EtOH ( 10 mL). The unreacted amino acid was precipitated and filtered off. The filtrate was concentrated to give the crude desired product which was used directly in the next step. MS: 142. 1 (M- l )'.

Yield	Reaction Conditions	Operation in experiment
100%	With thionyl chloride; at -5 - 20℃; for 6h;	Absolute ethanol (300 mL) was cooled at -5°C then thionyl chloride (14.01 mL, 192.1 mmol) was added keeping the temperature below 0°C, followed by portionwise addiction of (S)-6- oxopiperidine-2-carboxylic acid (25.0 g, 174.6 mmol). The mixture was stirred at room temperature for 6 hours. The solvent was evaporated, then toluene (300 mL) and Et3N (48.7 mL) were added. After 0.5 hour the precipitate was filtered and washed with toluene and Et20. The filtrate was evaporated and the residue treated with Et20. The precipitate was eliminated and the solution was concentrated to give the title compound as yellow oil. Yield (29.9 g, 100percent). H NMR (400 MHz, CDCI3): delta 1 .30 (t, 3H), 1 .75-1 .95 (m, 3H), 2.15-2.25 (m, 1 H), 2.30-2.45 (m, 2H), 4.08 (m, 1 H), 4.24 (q, 2H), 6.43 (br s, 1 H). D2)
100%	With thionyl chloride; at 20℃; for 6h;	Absolute ethanol (300 mL) was cooled at ?5° C. then thionyl chloride (14.01 mL, 192.1 mmol) was added keeping the temperature below 0° C., followed by portionwise addiction of <strong>[34622-39-4](S)-6-oxopiperidine-2-carboxylic acid</strong> (25.0 g, 174.6 mmol). The mixture was stirred at room temperature for 6 hours. The solvent was evaporated, then toluene (300 mL) and Et3N (48.7 mL) were added. After 0.5 hour the precipitate was filtered and washed with toluene and Et2O. The filtrate was evaporated and the residue treated with Et2O. The precipitate was eliminated and the solution was concentrated to give the title compound as yellow oil. Yield (29.9 g, 100percent). [0132] 1H NMR (400 MHz, CDCl3): delta 1.30 (t, 3H), 1.75-1.95 (m, 3H), 2.15-2.25 (m, 1H), 2.30-2.45 (m, 2H), 4.08 (m, 1H), 4.24 (q, 2H), 6.43 (br s, 1H).
	With thionyl chloride; at 20℃; for 16.5h;	Step I-1: Ethyl (25)-6-oxo-2-piperidinecarboxylate. To a solution of 6-oxo-L-picolinic acid (5.0Og, 34.9 mmol) in 120 mL EtOH added thionyl chloride (25.5 mL, 349 mmol) in 1 mL aliquots over 30 minutes. After 16 hours of stirring at room temperature, the reaction mixture was concentrated to obtain the desired product containing unidentified impurities as a yellow oil. MS: M+H = 172. The product was used in Step 1-2 without further purification.

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

Yield	Reaction Conditions	Operation in experiment
45%	With water; acetic acid; for 3h;Inert atmosphere; Reflux;	(a) (S)-6-Oxo-piperidine-2-carboxylic acid A mixture of (S)-2-amino-hexanedioic acid (50 g, 310.25 mmol), acetic acid (100 mL), and water (400 mL) water was refluxed for 3 h. The unchanged starting amino acid was filtered off (24 g) and the filtrate evaporated, dissolved in hot water (50 mL) and then cooled. A crystalline precipitate formed which was filtered to provide the title intermediate (20 g, 45percent yield).
	In ethanol;	Step A. (S)-6-Oxopiperidine-2-carboxylic acid A solution of (S)-2-aminohexanedioic acid (470 mg, 2.9 mmol) in 20percent AcOH (5 mL) was stirred at 110° C. overnight. The solvent was removed in vacuo and the residue was dissolved in EtOH (10 mL). The unreacted amino acid was precipitated and filtered off. The filtrate was concentrated to give the crude desired product which was used directly in the next step. MS: 142.1 (M-1)-.
	With acetic acid; at 110℃;	Example 6. Preparation of (S)-N-((S)-l-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl) - amino)-2-oxoethyl)-N-(3-fluorophenyl)-6-oxo-l-(pyrimidin-2-yl)piperidine-2-carboxamide Compounds 19 and 20 were prepared according to the following scheme, using the following protocol. Step A. (S)-6-Oxopiperidine-2-carboxylic acid. A solution of (S)-2-aminohexanedioic acid (470 mg, 2.9 mmol) in 20percent AcOH (5 niL) was stirred at 1 10 °C overnight. The solvent was removed in vacuo and the residue was dissolved in EtOH (10 mL). The unreacted amino acid was precipitated and filtered off. The filtrate was concentrated to give the crude desired product which was used directly in the next step. MS: 142.1 (M-l)\

Yield	Reaction Conditions	Operation in experiment
		Step (b): Preparation of S-HPCA.DAA Salt Dissolve 1 g. of the product in 26 ml. of acetone containing 5percent of water at reflux. Allow to cool, seeding with S-HPCA.DAA salt. Filter the salt which precipitates, wash with acetone containing 5percent of water, acetone, and air dry to obtain 0.25 g. of S-HPCA.DAA salt, m.p. 194.5°-198° C.
		Air dry to obtain 2.61 g. (26.1percent) of S-HPCA.DAA, m.p. 191°-194° C. (inserted at 160°).
		Step (b): Preparation of S-6-oxo-2-piperidinecarboxylic Acid (S-HPCA) Employing substantially the same procedure as described in Example 1, Step (c), S-HPCA.DAA salt is converted to optically pure S-6-oxo-2-piperidine carboxylic acid (S-HPCA).

[ CAS No. 34622-39-4 ] {[proInfo.proName]}

Quality Control of [ 34622-39-4 ]

Related Doc. of [ 34622-39-4 ]

Product Details of [ 34622-39-4 ]

Calculated chemistry of [ 34622-39-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 34622-39-4 ]

Application In Synthesis of [ 34622-39-4 ]

[ 34622-39-4 ] Synthesis Path-Upstream 1~11

[ 34622-39-4 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry