[ CAS No. 106825-81-4 ] {[proInfo.proName]}

Name: 106825-81-4|(R)-3-Morpholinecarboxylic Acid|95%
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Quality Control of [ 106825-81-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 106825-81-4 ]

Product Details of [ 106825-81-4 ]

CAS No. :	106825-81-4	MDL No. :	MFCD03426306
Formula :	C₅H₉NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JUNOWSHJELIDQP-SCSAIBSYSA-N
M.W :	131.13	Pubchem ID :	12680089
Synonyms :

Calculated chemistry of [ 106825-81-4 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.8
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	33.61
TPSA :	58.56 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) :	-9.39 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.75
Log Po/w (XLOGP3) :	-3.23
Log Po/w (WLOGP) :	-1.32
Log Po/w (MLOGP) :	-3.44
Log Po/w (SILICOS-IT) :	-0.05
Consensus Log Po/w :	-1.46

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	1.45
Solubility :	3680.0 mg/ml ; 28.0 mol/l
Class :	Highly soluble
Log S (Ali) :	2.57
Solubility :	48800.0 mg/ml ; 372.0 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	0.11
Solubility :	170.0 mg/ml ; 1.29 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.23

Safety of [ 106825-81-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 106825-81-4 ]

* 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.

Downstream synthetic route of [ 106825-81-4 ]

[ 106825-81-4 ] Synthesis Path-Downstream 1~7

1
[ CAS Unavailable ]
[ 106825-81-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In methanol at 64℃; for 7h;

Reference： [1]Kogami; Okawa [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 8, p. 2963 - 2965]

2
[ 106825-80-3 ]
[ 106825-81-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: H₂ / Pd black / methanol / 0.5 h 2: Et₃N / methanol / 7 h / 64 °C

Reference： [1]Kogami; Okawa [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 8, p. 2963 - 2965]

3
[ 1446358-48-0 ]
[ 106825-81-4 ]
[ 1628728-20-0 ]

Yield	Reaction Conditions	Operation in experiment
48%	With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; water at 90℃; for 18h;	1 General procedure: General procedure B A solution of amino nucleophile (3 equiv.), triethylamine (10 equiv.), and Intermediate 1 (1 equiv.) was stirred in dioxane and water (2:1 ratio) at 90 °C until complete consumption of starting material was observed by LC/MS. The solution was diluted withiN hydrochloric acid and dichloromethane. The layers were then separated and thelayer was extracted with dichloromethane. The organics were combined, dried over magnesium sulfate, filtered, and the solvent was removed in vacuo. Purification yielded theproductThe title compound was prepared following general procedure B, except (R)-morpholine-3-carboxylic acid (4 equiv.) was the amine reactant, Hunig’s base (5 equiv.) was used instead of triethylamine, and the contents were heated to 90 °C for 18 h as a solution in THF/water (9:1). Solvent was removed under a stream of nitrogen, and the crude material was purified via reverse phase HPLC using a 20-51% acetonitrile/water (in 0.1% TFA) gradient to deliver the desired compound, Compound 1-95 (19 mg, 76% yield). 1H NMR (500 MHz, CD3OD) ö 8.81 (d, 1 H), 8.39 (d, 1 H), 7.57 (s, 1 H), 7.26 - 7.34 (m, 1 H),7.02 - 7.16 (m, 2 H), 6.93 (d, 2 H), 6.00 (s, 2 H), 5.26 - 5.59 (m, 1 H), 4.55 (d, 2 H), 4.04 (s, 1 H), 3.93 (dd, 1 H), 3.62 - 3.80 (m, 2 H).

Reference： [1]Current Patent Assignee: CYCLERION THERAPEUTICS INC - WO2014/144100, 2014, A2 Location in patent: Paragraph 00274

4
[ 82911-69-1 ]
[ 106825-81-4 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
3.19 g	With sodium hydrogencarbonate In tetrahydrofuran; water for 28h;	Preparation of (R)-4-(((9H-fluoren-9-yl)methoxy)carbonyl)morpholine-3-carboxylic acid To a solution of (R)-morpholine-3-carboxylic acid (2 g, 15.25 mmol) in THF (50.8 mL) and water (25.4 mL) was added sodium bicarbonate (1.922 g, 22.88 mmol) and FMOC-OSU (5.14 g, 15.25 mmol). The resulting mixture was stirred for 28 h. Afterremoval of THF, the white suspension was diluted with sat.NaHCO3/water and ether.Filter through celite. Washed with water and ether. Separate ether and aqueous layer.The aqueous layer was acidified with 1 N HC1, extracted with ethyl acetate, washed withbrine, dried over Na2504, concentrated to give 3.19 g (R)-4-(((9H-fluoren-9-yl)methoxy)carbonyl)morpholine-3 -carboxylic acid as white solid.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2016/39749, 2016, A1 Location in patent: Page/Page column 884; 885

5
[ 1786425-01-1 ]
[ 106825-81-4 ]
[ 2210228-83-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In ethanol at 25℃; Inert atmosphere;

Reference： [1]Ren, Qingyun; Liu, Xinchang; Yan, Guanghua; Nie, Biao; Zou, Zhifu; Li, Jing; Chen, Yunfu; Wei, Yu; Huang, Jianzhou; Luo, Zhonghua; Gu, Baohua; Goldmann, Siegfried; Zhang, Jiancun; Zhang, Yingjun [Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 1355 - 1374]

6
[ 1810863-44-5 ]
[ 106825-81-4 ]
[ 2205016-12-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In ethanol at 25℃; Inert atmosphere;

7
[ CAS Unavailable ]
[ 106825-81-4 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
25.22%	Stage #1: 2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a,10b-dimethyl-8-methylidenedecahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)acetaldehyde; (3R)-morpholine-3-carboxylic acid With acetic acid In tetrahydrofuran at 45℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 45℃; for 8h;	(3R)-4-(2-((3R,4aR,6aS,7R,10bR))-3-cyclopentyl-6a,10b-dimethyl-8-methylene-decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethyl)morpholine-3-carboxylic acid Step 1 (3R)-4-(2-((3R,4aR,6aS,7R,10bR))-3-cyclopentyl-6a,10b-dimethyl-8-methylene-decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethyl)morpholine-3-carboxylic acid 2-((3R,4aR,6aS,7R,10bR)-3-cyclopentyl-6a,10b-dimethyl-8-methylene-decahydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)acetaldehyde (250.00 mg, 721.50 umol) was dissolved in tetrahydrofuran (20 mL), and (3R)-morpholine-3-carboxylic acid (100.29 mg, 764.79 umol) and acetic acid (525.00 mg, 8.74 mmol, 500.00 uL) were added successively, then stirred at 45° C. for 1 hour. Sodium borohydride-acetic acid (500.00 mg, 2.36 mmol) was added and stirred at 45° C. for 8 hours. The system was concentrated. The residue was separated by column chromatography (silica, dichloromethane/methanol=20/1 to 10/1) to give (3R)-4-(2-((3R,4aR,6aS,7R,10bR))-3-cyclopentyl-6a,10b-dimethyl-8-methylene-deca hydro-1H-naphtho[2,1-d][1,3]dioxin-7-yl)ethyl)morpholine-3-carboxylic acid 456 (84 mg, yield: 25.22%). MS m/z (ESI):462.1 [M+1] 1H NMR (400 MHz, MeOD) 4.88-4.83 (m, 1H), 4.76 (s, 1H), 4.70 (d, J=5.5 Hz, 1H), 4.16 (d, J=10.5 Hz, 1H), 4.08 (d, J=11.3 Hz, 1H), 4.01 (d, J=12.3 Hz, 1H), 3.78 (t, J=11.4 Hz, 1H), 3.69 (t, J=10.9 Hz, 1H), 3.55-3.42 (m, 3H), 3.02 (t, J=9.8 Hz, 1H), 2.75 (br. s., 1H), 2.49-2.30 (m, 2H), 2.24-1.38 (m, 18H), 1.35 (s, 3H), 1.31-1.21 (m, 3H), 0.84 (s, 3H).

Reference： [1]Current Patent Assignee: WUXI APPTEC CO., LTD.; HEILONGJIANG ZBD PHARMACEUTICAL CO LTD - US2018/346438, 2018, A1 Location in patent: Paragraph 0519-0522

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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.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
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Code	Phrase
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P391	Collect spillage. Hazardous to the aquatic environment
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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.
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P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
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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
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H221	Flammable gas
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H223	Flammable aerosol
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H226	Flammable liquid and vapour
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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
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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. 106825-81-4 ] {[proInfo.proName]}

Quality Control of [ 106825-81-4 ]

Related Doc. of [ 106825-81-4 ]

Product Details of [ 106825-81-4 ]

Calculated chemistry of [ 106825-81-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 106825-81-4 ]

Application In Synthesis of [ 106825-81-4 ]

[ 106825-81-4 ] Synthesis Path-Downstream 1~7

Related Functional Groups of [ 106825-81-4 ]

Carboxylic Acids

Related Parent Nucleus of [ 106825-81-4 ]

Morpholines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 106825-81-4 ]

Related Parent Nucleus of
[ 106825-81-4 ]