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Basic Information
CAS No.: 181289-33-8
Name: (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid
Molecular Structure:
Molecular Structure of 181289-33-8 ((R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid)
Formula: C9H17NO3
Molecular Weight: 187.239
Synonyms: Hexanoicacid, 3-(2-amino-2-oxoethyl)-5-methyl-, (R)-;
EINECS: 605-923-8
Density: 1.081 g/cm3
Melting Point: 128-133 °C
Boiling Point: 401.929 °C at 760 mmHg
Flash Point: 196.88 °C
PSA: 80.39000
LogP: 1.69910
Synthetic route

1‐phenylethan‐1‐amine 3‐(carbamoylmethyl)‐5‐methylhexanoate

181289-33-8

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

Conditions
ConditionsYield
Stage #1: 1‐phenylethan‐1‐amine 3‐(carbamoylmethyl)‐5‐methylhexanoate With hydrogenchloride In water at 10 - 30℃; for 2h; pH=0.5 - 2;
Stage #2: With sulfuric acid In water at 6 - 40℃; for 3h; pH=1.5; Temperature; Reagent/catalyst; Solvent;
100%

3-isobutylglutarimide

181289-33-8

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

Conditions
ConditionsYield
With water In tetrahydrofuran at 45℃; for 15h; Reagent/catalyst; Solvent; Temperature;96.1%
1403953-91-2

(3S)-3-(2-(allyloxy)-2-oxoethyl)-5-methylhexanoic acid

181289-33-8

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

Conditions
ConditionsYield
Stage #1: (3S)-3-(2-(allyloxy)-2-oxoethyl)-5-methylhexanoic acid With magnesium nitride In methanol at 20 - 80℃; for 16h;
Stage #2: With hydrogenchloride In methanol; water pH=3 - 4;
93%
181289-15-6

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

181289-33-8

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

Conditions
ConditionsYield
With D-phenylglycine butyl ester In isopropyl alcohol Heating;90.39%
With (R)-1-phenyl-ethyl-amine In methanol; chloroform at 25 - 40℃; for 3.16h; Solvent; Temperature;41%
Stage #1: (±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid With (R)-1-phenyl-ethyl-amine In ethanol; chloroform for 0.75h; Reflux;
Stage #2: With hydrogenchloride In ethanol; chloroform; water for 0.75h; Cooling;
40%
1237492-10-2

(-)-3-cyclohexylsulfanylcarbonylmethyl-5-methyl-hexanoic acid

181289-33-8

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

Conditions
ConditionsYield
With ammonia In water at 40℃;88%
1082077-07-3

(3S)-3-(2-ethoxy-2-oxoethyl)-5-methylhexanoic acid

181289-33-8

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

Conditions
ConditionsYield
Stage #1: (3S)-3-(2-ethoxy-2-oxoethyl)-5-methylhexanoic acid With ammonium iodide; sodium amide In tetrahydrofuran at 20℃; for 4h; Cooling with ice; Green chemistry;
Stage #2: With hydrogenchloride In water pH=4 - 5; Reagent/catalyst; Solvent; Green chemistry;
86.7%
With ammonia; calcium chloride In methanol at 55 - 60℃; under 3000.3 - 3375.34 Torr; Autoclave;
With ammonia; calcium chloride In methanol at 25 - 70℃; under 375.038 - 2250.23 Torr; Autoclave;
181289-25-8

(3S)-3-(2-methoxy-2-oxoethyl)-5-methylhexanoic acid

181289-33-8

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

Conditions
ConditionsYield
Stage #1: (3S)-3-(2-methoxy-2-oxoethyl)-5-methylhexanoic acid With ammonia In water at 20 - 80℃; under 760.051 - 1520.1 Torr; for 6 - 92h;
Stage #2: With hydrogenchloride In water pH=1 - 3; Product distribution / selectivity;
60%
Stage #1: (3S)-3-(2-methoxy-2-oxoethyl)-5-methylhexanoic acid With ammonia; ammonium chloride In water at 20 - 40℃; for 42.5h;
Stage #2: With hydrogenchloride In water pH=4; Product distribution / selectivity;
Stage #1: (3S)-3-(2-methoxy-2-oxoethyl)-5-methylhexanoic acid With ammonia In water; toluene at 20℃; for 88h;
Stage #2: With sulfuric acid In water pH=3; Product distribution / selectivity;
With ammonium hydroxide at 25 - 90℃; for 75h; Reagent/catalyst; Temperature;75 g
930585-94-7

(3R)-5-methyl-3-(2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)hexanoic acid

181289-33-8

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

Conditions
ConditionsYield
Stage #1: (3R)-5-methyl-3-(2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)hexanoic acid With ammonia; water; lithium In tetrahydrofuran at -40℃; for 6 - 10h;
Stage #2: With hydrogenchloride In water pH=1.5 - 1.7; Product distribution / selectivity;
59.37%
Stage #1: (3R)-5-methyl-3-(2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)hexanoic acid With ammonia; water; sodium In tetrahydrofuran at -40℃; for 6 - 10h;
Stage #2: With hydrogenchloride In water pH=1.5 - 1.7; Product distribution / selectivity;
39.37%
With sulfuric acid In tetrahydrofuran at 25 - 30℃; Product distribution / selectivity;39%
With palladium 10% on activated carbon; hydrogen In methanol at 30℃; under 7500.75 Torr; for 12h; Autoclave; Industrial scale;
1385049-51-3

R-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid 1-phenylpropylamine salt

181289-33-8

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

Conditions
ConditionsYield
Stage #1: R-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid 1-phenylpropylamine salt With ammonia In water at 80℃; for 5h;
Stage #2: With hydrogenchloride In water at 0℃; pH=1;
53%

(R)-methyl 3-(carbamoylmethyl)-5-methylhexanoate

181289-33-8

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

Conditions
ConditionsYield
Stage #1: (R)-methyl 3-(carbamoylmethyl)-5-methylhexanoate With hydrogenchloride In water at 20 - 25℃; for 1 - 10h;
Stage #2: With sodium hydroxide In water pH=3; Product distribution / selectivity;
Stage #1: (R)-methyl 3-(carbamoylmethyl)-5-methylhexanoate With hydrogenchloride; water at 20 - 25℃;
Stage #2: With sodium hydroxide In water pH=3;
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    Product Name: (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid CAS: 181289-33-8 MF: C9H17NO3 MW: 187.24 EINECS: 605-923-8 Mol File: 181289-33-8.mol (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid Structure (R)-(-)-3-Carbamoymethyl-5-

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Specification

The (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid is an organic compound with the formula C9H17NO3. The systematic name of this chemical is (3R)-3-(2-amino-2-oxoethyl)-5-methylhexanoic acid. With the CAS registry number 181289-33-8, it is also named as hexanoic acid, 3-(2-amino-2-oxoethyl)-5-methyl-, (3R)-. The product's categories are Intermidiate of Pregablin; Starting Raw Materials & Intermediates. In addition, the molecular weight is 187.24. 

The other characteristics of (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid can be summarized as: (1)ACD/LogP: 0.60; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0; (4)ACD/LogD (pH 7.4): -2; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 5; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 80.39 Å2; (13)Index of Refraction: 1.475; (14)Molar Refractivity: 48.791 cm3; (15)Molar Volume: 173.272 cm3; (16)Polarizability: 19.342×10-24 cm3; (17)Surface Tension: 41.913 dyne/cm; (18)Density: 1.081 g/cm3; (19)Flash Point: 196.88 °C; (20)Enthalpy of Vaporization: 71.66 kJ/mol; (21)Boiling Point: 401.929 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

People can use the following data to convert to the molecule structure. 
1. SMILES:CC(C)C[C@H](CC(N)=O)CC(O)=O
2. InChI:InChI=1/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)/t7-/m1/s1
3. InChIKey:NPDKTSLVWGFPQG-SSDOTTSWBV
4. 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)/t7-/m1/s1
5. Std. InChIKey:NPDKTSLVWGFPQG-SSDOTTSWSA-N