[ CAS No. 760-58-7 ]

Name: 2-Cyano-4-methylpent-2-enoic acid
Brand: Ambeed
SKU: A191057
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Quality Control of [ 760-58-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 760-58-7 ]

SDS

Product Details of [ 760-58-7 ]

CAS No. :	760-58-7	MDL No. :	MFCD22377852
Formula :	C₇H₉NO₂	Boiling Point :	283.1°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	139.15	Pubchem ID :	-
Synonyms :

Computed Properties of [ 760-58-7 ]

TPSA :Topological Polar Surface Area	61.1	H-Bond Acceptor Count :	3
XLogP3 :	1.3	H-Bond Donor Count :	1
SP3 :	0.43	Rotatable Bond Count :	2

Safety of [ 760-58-7 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P280	UN#:	N/A
Hazard Statements:	H302+H312+H332	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 760-58-7 ]

Upstream synthesis route of [ 760-58-7 ]
Downstream synthetic route of [ 760-58-7 ]

[ 760-58-7 ] Synthesis Path-Upstream 1~2

1
[ 372-09-8 ]
[ 78-84-2 ]
[ 760-58-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With ammonium acetate In tolueneReflux	Step 1 - 2-Cyano-4-methyl-2-pentenoic acidA stirred suspension of cyanoacetic acid (42.5g, 0.5 mol), ammonium acetate(1 .56g, 0.02 mol, 4 molpercent) and isobutyraldehyde (55ml, 39.66g, 0.55 mol, 1 .1 eq) in toluene (130ml) was heated to reflux with Dean-Stark removal of water. When generation of water ceased, the reaction mixture was cooled to room temperature and concentrated under reduced pressure to give a yellow solid (79.5g). Hexane (150ml) was added and the suspension was stirred at 400rpm for 1 hour. The solid was filtered, washed with hexane (2 x 50ml) and dried to provide the title compound as a yellow crystalline solid (58.5g, 83percent yield).
11.2 g	Stage #1: for 30.00 h; Stage #2: With piperidine In methanol for 1.00 h;	To a solution of 2-cyanoacetic acid (8.7g, 102 mmol) in methanol (200mL) was added 2-methylpropanal (18.6 mL, 204 mmol) and the solution was stirred with a slight exotherm noted. After 30 minutes, added piperidine (1 1.1 mL, 1 12 mmol) and continued stirring for 1 h before removing solvent in vacuo with gentle heating. The thick material was diluted with ether and washed with 125mL of 1.0M HC1 and then washed with brine. The organic phase was dried over sodium sulfate and concentrated to afford a colorless oil weighing 11.2 g of 2- cyano-4-methylpent-2-enoic acid which precipitated on standing.

Reference： [1] Organic Process Research and Development, 2014, vol. 18, # 1, p. 109 - 121
[2] Patent: WO2012/25861, 2012, A1. Location in patent: Page/Page column 22
[3] Journal of the Chemical Society, 1932, p. 445,453[4] Journal of the Chemical Society, 1933, p. 613
[5] Patent: WO2014/39899, 2014, A1. Location in patent: Page/Page column 52
[6] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 101, p. 67 - 72

2
[ 372-09-8 ]
[ 590-86-3 ]
[ 760-58-7 ]

Reference： [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 8, p. 1878 - 1882

[ 760-58-7 ] Synthesis Path-Downstream 1~10

2
[ 372-09-8 ]
[ 78-84-2 ]
[ 760-58-7 ]

Yield	Reaction Conditions	Operation in experiment
89%	With pyrrolidine; pyridine; at 20℃;	Into a 100-mL round-bottom flask, was placed 2-cyanoacetic acid (2 g, 23.51 mmol, 1.00 eq.), pyridine (10 mL), 2-methylpropanal (1.85 g, 25.66 mmol, 1.09 eq.), pyrrolidine (400 mg, 5.62 mmol, 0.24 eq.). The resulting solution was stirred for 1.5 h at rt. The reaction was then quenched by the addition of hydrogen chloride:H20 (12:20 mL). The resulting solution was extracted with ethyl acetate (2 x 20 mL). The organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 2.9 g (89%) of 2-cyano-4-methylpent-2-enoic acid as a light yellow solid.
83%	With ammonium acetate; In toluene;Reflux;	Step 1 - 2-Cyano-4-methyl-2-pentenoic acidA stirred suspension of cyanoacetic acid (42.5g, 0.5 mol), ammonium acetate(1 .56g, 0.02 mol, 4 mol%) and isobutyraldehyde (55ml, 39.66g, 0.55 mol, 1 .1 eq) in toluene (130ml) was heated to reflux with Dean-Stark removal of water. When generation of water ceased, the reaction mixture was cooled to room temperature and concentrated under reduced pressure to give a yellow solid (79.5g). Hexane (150ml) was added and the suspension was stirred at 400rpm for 1 hour. The solid was filtered, washed with hexane (2 x 50ml) and dried to provide the title compound as a yellow crystalline solid (58.5g, 83% yield).
11.2 g		To a solution of 2-cyanoacetic acid (8.7g, 102 mmol) in methanol (200mL) was added 2-methylpropanal (18.6 mL, 204 mmol) and the solution was stirred with a slight exotherm noted. After 30 minutes, added piperidine (1 1.1 mL, 1 12 mmol) and continued stirring for 1 h before removing solvent in vacuo with gentle heating. The thick material was diluted with ether and washed with 125mL of 1.0M HC1 and then washed with brine. The organic phase was dried over sodium sulfate and concentrated to afford a colorless oil weighing 11.2 g of 2- cyano-4-methylpent-2-enoic acid which precipitated on standing.

Reference： [1]Organic Process Research and Development,2014,vol. 18,p. 109 - 121
[2]Patent: WO2019/99582,2019,A1.Location in patent: Paragraph 0336; 0339; 0347; 0350
[3]Patent: WO2012/25861,2012,A1.Location in patent: Page/Page column 22
[4]Journal of the Chemical Society,1932,p. 445,453
Journal of the Chemical Society,1933,p. 613
[5]Patent: WO2014/39899,2014,A1.Location in patent: Page/Page column 52
[6]Journal of Molecular Catalysis B: Enzymatic,2014,vol. 101,p. 67 - 72

3
[ 120-15-0 ]
[ 760-58-7 ]
2-(6-methoxy-1,2,3,4-tetrahydroquinoline-1-carbonyl)-4-methylpent-2-enenitrile [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 11385 - 11389
Angew. Chem.,2019,vol. 131,p. 11507 - 11511,5

4
[ 760-58-7 ]
(S)-6-amino-N-((R)-2-phenyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)ethyl)-2-((2,2,2-trifluoroethyl)amino)hexanamide hydrochloride [ No CAS ]
((R)-1-((S)-6-(2-cyano-4-methylpent-2-enamido)-2-((2,2,2-trifluoroethyl)amino)hexanamido)-2-phenylethyl)boronic acid [ No CAS ]

Reference： [1]Patent: WO2019/99582,2019,A1

5
[ 760-58-7 ]
(S)-6-amino-N-((R)-2-phenyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)ethyl)-2-((2,2,2-trifluoroethyl)amino)hexanamide hydrochloride [ No CAS ]
(S)-6-(2-cyano-4-methylpent-2-enamido)-N-((R)-2-phenyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)ethyl)-2-((2,2,2-trifluoroethyl)amino)hexanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
400 mg	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; at 0 - 20℃;	DIPEA (0.96 g, 7.41 mmol) was added to a stirred solution of (S)-6-amino-N-((R)-2- phenyl-l-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d] [l,3,2]dioxaborol-2- yl)ethyl)-2-((2,2,2-trifluoroethyl)amino)hexanamide hydrochloride (1.35 g, 2.47 mmol), 2-cyano-4- methylpent-2-enoic acid (275 mg, 1.98 mmol) and BOP (1.092 g, 2.47 mmol) in DMF (10 mL) at 0 C. The mixture was stirred at rt for 2 h., then washed with brine (25 mL), dried over Na2S04 and concentrated in vacuo. The crude residue was purified by flash column chromatography with MeOH: dichlorome thane to afford (S)-6-(2-cyano-4-methylpent-2-enamido)-N-((R)-2-phenyl-l-((3aS,4S,6S,7aR)-3a,5,5- trimethylhexahydro-4,6-methanobenzo[d][l,3,2]dioxaborol-2-yl)ethyl)-2-((2,2,2- trifluoroethyl)amino)hexanamide as a white solid (400 mg, 25%).

Reference： [1]Patent: WO2019/99582,2019,A1.Location in patent: Paragraph 0259; 0263

6
[ 760-58-7 ]
(S)-2-acetamido-6-amino-N-((R)-2-phenyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)ethyl)hexanamide [ No CAS ]
((R)-1-((S)-2-acetamido-6-(2-cyano-4-methylpent-2-enamido)hexanamido)-2-phenylethyl)boronic acid [ No CAS ]

Reference： [1]Patent: WO2019/99582,2019,A1

7
[ 760-58-7 ]
(S)-2-acetamido-6-amino-N-((R)-2-phenyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)ethyl)hexanamide [ No CAS ]
(S)-2-acetamido-6-(2-cyano-4-methylpent-2-enamido)-N-((R)-2-phenyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)ethyl)hexanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
380 mg		To a solution of (S)-2-acetamido-6-amino-N-((R)-2-phenyl-l-((3aS,4S,6S,7aR)- 3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][l,3,2]dioxaborol-2-yl)ethyl)hexanamide (167 mg, 1.2 mmol) and DIPEA (390 mg, 3 mmol) in DMF (5 mL) at 0 C was added BOP (530 mg, 1.2 mmol). After stirring at 0 C for 1 h, <strong>[760-58-7]2-cyano-4-methylpent-2-enoic acid</strong> (470 mg, 1. mmol) was added. The resulting mixture was stirred at rt for 3 h, before being partitioned between HC1 (1M) and EtOAc. The organic layer was washed with aq. NaHC03, water and brine, dried over Na2S04 and filtrated. The filtrate was concentrated to dryness to afford (S)-2-acetamido-6-(2-cyano-4-methylpent-2-enamido)-N-((R)-2 -phenyl- l-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][l,3,2]dioxaborol-2- yl)ethyl)hexanamide as an off-white solid (380 mg, 65%).

Reference： [1]Patent: WO2019/99582,2019,A1.Location in patent: Paragraph 0254; 0256

8
[ 760-58-7 ]
(S)-6-amino-2-((2S,3R)-3-hydroxy-2-isobutyramidobutanamido)-N-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)hexanamide [ No CAS ]
((R)-1-((S)-6-(2-cyano-4-methylpent-2-enamido)-2-((2S,3R)-3-hydroxy-2-isobutyramidobutanamido)hexanamido)-3-methylbutyl)boronic acid [ No CAS ]

Reference： [1]Patent: WO2019/99582,2019,A1

9
[ 760-58-7 ]
(S)-6-amino-2-((2S,3R)-3-hydroxy-2-isobutyramidobutanamido)-N-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)hexanamide [ No CAS ]
(S)-6-(2-cyano-4-methylpent-2-enamido)-2-((2S,3R)-3-hydroxy-2-isobutyramidobutanamido)-N-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)hexanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.32 g	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	A solution of (S)-6-amino-2-((2S,3R)-3-hydroxy-2-isobutyramidobutanamido)-N- ((R)-3-methyl-l-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d] [l,3,2]dioxaborol-2- yl)butyl)hexanamide (1.6 g, 2.83 mmol), <strong>[760-58-7]2-cyano-4-methylpent-2-enoic acid</strong> (0.394 g, 2.83 mmol), HATU (1.18 g, 3.11 mmol) and TEA (0.571 g, 5.66 mmol) in DMF (10 mL) , was stirred at rt for 3 h under argon. Water (50 mL) was added, and the resulting mixture was extracted with ethyl acetate (3 x 30 mL). The combined organic layer was washed with brine (2 x 20 mL), dried over Na2S04, and concentrated in vacuo. The residue was purified by flash column (silica:200-300 mesh, eluted with DCM:MeOH (20: 1)) to afford (S)-6-(2-cyano-4-methylpent-2-enamido)-2-((2S,3R)-3-hydroxy-2-isobutyramidobutanamido)-N-((R)-3- methyl-l-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][l,3,2]dioxaborol-2- yl)butyl)hexanamide as a yellow solid (0.32 g, 17%).

Reference： [1]Patent: WO2019/99582,2019,A1.Location in patent: Paragraph 0243; 0251

10
[ 760-58-7 ]
1-[(1R)-2-phenyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^[2,6]]decan-4-yl]ethyl]-3-[(2S)-pyrrolidin-2-ylmethyl]urea [ No CAS ]
((R)-1-(3-(((S)-1-(2-cyano-4-methylpent-2-enoyl)pyrrolidin-2-yl)methyl)ureido)-2-phenylethyl)boronic acid [ No CAS ]

Reference： [1]Patent: WO2019/99582,2019,A1

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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
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

[ CAS No. 760-58-7 ]

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[ 760-58-7 ] Synthesis Path-Upstream 1~2

[ 760-58-7 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 760-58-7 ]

Nitriles

Alkenyls

Carboxylic Acids

Aliphatic Chain Hydrocarbons

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[ 760-58-7 ]