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3-Carbamoymethyl-5-methylhexanoic acid
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Name

3-Carbamoymethyl-5-methylhexanoic acid

 EINECS 605-922-2
CAS No. 181289-15-6 Density 1.08 g/cm3
PSA 80.39000 LogP 1.69910
Solubility N/A Melting Point 106-108 °C
Formula C9H17NO3 Boiling Point 401.9 °C at 760 mmHg
Molecular Weight 187.239 Flash Point 196.9 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 181289-15-6 (3-Carbamoymethyl-5-methylhexanoic acid) Hazard Symbols N/A
Synonyms

hexanoic acid, 3-(2-amino-2-oxoethyl)-5-methyl-;3-(2-Amino-2-oxoethyl)-5-methylhexanoic acid;

Article Data 16

3-Carbamoymethyl-5-methylhexanoic acid Synthetic route

185815-59-2

3-isobutylglutaric anhydride

181289-15-6

(±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid

Conditions
ConditionsYield
With ammonia In water at -10 - 40℃; for 1.5h;100%
With ammonium hydroxide at 10℃; for 2h; Temperature;95%
Stage #1: 3-isobutylglutaric anhydride With ammonia In tert-butyl methyl ether; water at 0 - 20℃;
Stage #2: With hydrogenchloride In tert-butyl methyl ether; water pH=2;		80.4%
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

181289-15-6

(±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid

Conditions
ConditionsYield
With urea In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 3h; Temperature; Solvent;93.5%
With pyridine; di-tert-butyl dicarbonate; ammonium bicarbonate In acetonitrile at 5 - 20℃; for 0.5h; Solvent;72.4%
With hydrogenchloride; ammonium hydroxide; acetic anhydride In tert-butyl methyl ether; water; ethyl acetate

3-isobutylglutarimide

181289-15-6

(±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid

Conditions
ConditionsYield
With potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene; water at 30℃; for 1h; Reagent/catalyst; Temperature;86.6%
Stage #1: 3-isobutylglutarimide With water; sodium hydroxide at 60℃; for 1h;
Stage #2: With hydrogenchloride; water		31 g
With sodium hydroxide at 50 - 90℃;

C10H15NO4

181289-15-6

(±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid

Conditions
ConditionsYield
With water; sodium hydroxide at 65℃; for 0.583333h; Temperature;79%

methyl 3-(2-amino-2-oxoethyl)-5-methylhexanoate

181289-15-6

(±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid

Conditions
ConditionsYield
With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 3h;76%
1385049-46-6

(1'SR,3 SR)-1-(1'-napthyl)ethyl-3-(carboxylomethyl)-5-methylhexanoate

181289-15-6

(±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid

Conditions
ConditionsYield
Stage #1: (1'SR,3 SR)-1-(1'-napthyl)ethyl-3-(carboxylomethyl)-5-methylhexanoate With chloroformic acid ethyl ester; triethylamine In acetone at -20℃; Inert atmosphere;
Stage #2: With ammonia In water; acetone at -20℃; for 2h;
Stage #3: With sodium hydroxide In water at 0℃;		58%
1634-04-4

tert-butyl methyl ether

181289-15-6

(±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid

Conditions
ConditionsYield
With ammonium hydroxide In water
181289-34-9

(S)‑3‑carbamoylmethyl‑5‑methylhexanoic acid

181289-15-6

(±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid

Conditions
ConditionsYield
Stage #1: (S)‑3‑carbamoylmethyl‑5‑methylhexanoic acid With toluene-4-sulfonic acid In toluene Reflux;
Stage #2: With sodium hydroxide In water; toluene at 25 - 65℃;
Stage #3: With hydrogenchloride In water at 10 - 15℃; for 1.5h; Product distribution / selectivity;
590-86-3

isovaleraldehyde

181289-15-6

(±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: di-n-propylamine; ethyl 2-cyanoacetate / cyclohexane / 2 h / 25 - 30 °C / Reflux
1.2: 5.17 h / 25 - 50 °C
1.3: 48 h / Reflux
2.1: urea / 12 h / 130 - 135 °C
2.2: 60 - 90 °C
View Scheme
Multi-step reaction with 5 steps
1.1: piperidine; pyridine; acetic acid / hexane / 48 h / Reflux; Inert atmosphere
2.1: di-n-propylamine / 16 h / 15 - 55 °C
3.1: hydrogen bromide / water / 72 h / 100 °C
4.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere
5.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C
5.2: pH 2
View Scheme
Multi-step reaction with 6 steps
1.1: piperidine; pyridine; acetic acid / hexane / 48 h / Reflux; Inert atmosphere
2.1: di-n-propylamine / 16 h / 15 - 55 °C
3.1: hydrogen bromide / water / 72 h / 100 °C
4.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere
5.1: 1,4-diaza-bicyclo[2.2.2]octane / tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere
6.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere
6.2: 2 h / -20 °C
6.3: 0 °C
View Scheme
Multi-step reaction with 4 steps
1: tetramethyl ammoniumhydroxide; trimethyldodecylammonium chloride / ethanol / 6 h / 25 °C
2: water; hydrogenchloride / 30 h / 140 °C / pH 1 - 2
3: acetic anhydride / 2 h / 120 °C
4: ammonium hydroxide / 2 h / 10 °C
View Scheme
Multi-step reaction with 4 steps
1.1: piperidine / hexane / 100 °C / Dean-Stark
2.1: piperidine / 2 h / 55 °C
2.2: 72 h / 100 - 120 °C
3.1: 5 h / 160 °C
4.1: sodium hydroxide; water / 0.58 h / 65 °C
View Scheme
51615-30-6

diethyl 2-(3-methylbutylidene)malonate

181289-15-6

(±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: di-n-propylamine / 16 h / 15 - 55 °C
2.1: hydrogen bromide / water / 72 h / 100 °C
3.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere
4.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C
4.2: pH 2
View Scheme
Multi-step reaction with 5 steps
1.1: di-n-propylamine / 16 h / 15 - 55 °C
2.1: hydrogen bromide / water / 72 h / 100 °C
3.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere
4.1: 1,4-diaza-bicyclo[2.2.2]octane / tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere
5.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere
5.2: 2 h / -20 °C
5.3: 0 °C
View Scheme

3-Carbamoymethyl-5-methylhexanoic acid Specification

3-Carbamoymethyl-5-methylhexanoic acid, with CAS number of 181289-15-6, can be called hexanoic acid, 3-(2-amino-2-oxoethyl)-5-methyl-; 3-(2-Amino-2-oxoethyl)-5-methylhexanoic acid; 3-(Carbamoylmethyl)-5-Methylhexanoic Acid. It belongs to the Product Categories of intermidiate of Pregablin; Pharmaceutical material and intermeidates; APIs Intermediate

Physical properties about 3-Carbamoymethyl-5-methylhexanoic acid are: (1)ACD/LogP: 0.476; (2)ACD/LogD (pH 5.5): -0.46; (3)ACD/LogD (pH 7.4): -2.26; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 5.07; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 4; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 6; (11)Index of Refraction: 1.475; (12)Molar Refractivity: 48.791 cm3; (13)Molar Volume: 173.272 cm3; (14)Polarizability: 19.342 10-24cm3; (15)Surface Tension: 41.9129981994629 dyne/cm; (16)Density: 1.081 g/cm3; (17)Flash Point: 196.88 °C; (18)Enthalpy of Vaporization: 71.66 kJ/mol; (19)Boiling Point: 401.929 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)SMILES:O=C(N)CC(CC(C)C)CC(=O)O;
(2)Std. InChI:InChI=1S/C9H17NO3/c1-6(2)3-7(4-8(10)11)5-9(12)13/h6-7H,3-5H2,1-2H3,(H2,10,11)(H,12,13);
(3)Std. InChIKey:NPDKTSLVWGFPQG-UHFFFAOYSA-N

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