Product Name

  • Name

    (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid

  • EINECS 605-923-8
  • CAS No. 181289-33-8
  • Article Data23
  • CAS DataBase
  • Density 1.081 g/cm3
  • Solubility
  • Melting Point 128-133 °C
  • Formula C9H17NO3
  • Boiling Point 401.929 °C at 760 mmHg
  • Molecular Weight 187.239
  • Flash Point 196.88 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 181289-33-8 ((R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid)
  • Hazard Symbols
  • Synonyms Hexanoicacid, 3-(2-amino-2-oxoethyl)-5-methyl-, (R)-;
  • PSA 80.39000
  • LogP 1.69910

Synthetic route

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

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

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

3-isobutylglutarimide

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
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%
(3S)-3-(2-(allyloxy)-2-oxoethyl)-5-methylhexanoic acid
1403953-91-2

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

(3R)‐3‐(carbamoylmethyl)‐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%
(±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid
181289-15-6

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

(3R)‐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%
(-)-3-cyclohexylsulfanylcarbonylmethyl-5-methyl-hexanoic acid
1237492-10-2

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

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
181289-33-8

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

Conditions
ConditionsYield
With ammonia In water at 40℃;88%
(3S)-3-(2-ethoxy-2-oxoethyl)-5-methylhexanoic acid
1082077-07-3

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

(3R)‐3‐(carbamoylmethyl)‐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;
(3S)-3-(2-methoxy-2-oxoethyl)-5-methylhexanoic acid
181289-25-8

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

(3R)‐3‐(carbamoylmethyl)‐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
(3R)-5-methyl-3-(2-oxo-2-{[(1R)-1-phenylethyl]amino}ethyl)hexanoic acid
930585-94-7

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

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic 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;
R-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid 1-phenylpropylamine salt
1385049-51-3

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

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

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

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
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;
methanol
67-56-1

methanol

3-isobutylglutaric anhydride
185815-59-2

3-isobutylglutaric anhydride

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
181289-33-8

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

Conditions
ConditionsYield
Stage #1: methanol; 3-isobutylglutaric anhydride With quinidine at -50℃; for 17h;
Stage #2: With ammonia In water at 20 - 40℃; for 72h;
Stage #3: With hydrogenchloride In water pH=3; Product distribution / selectivity;
(R)-(-)-phenylglycinol salt of (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid
1001296-65-6

(R)-(-)-phenylglycinol salt of (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
181289-33-8

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

Conditions
ConditionsYield
With hydrogenchloride In water at 60 - 62℃;n/a
(R)-3-(carbamoylmethyl)-5-methylhexanoic acid (R)-(+)-α-phenylethylamine
185815-61-6

(R)-3-(carbamoylmethyl)-5-methylhexanoic acid (R)-(+)-α-phenylethylamine

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
181289-33-8

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

Conditions
ConditionsYield
With hydrogenchloride In water at 31℃; pH=1.7;
With hydrogenchloride In water at 20 - 25℃; for 1.47h;
With hydrogenchloride In water pH=1 - 2;1.21 g
(±)‑3‑(carbamoylmethyl)‑5‑methylhexanoic acid
181289-15-6

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

A

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
181289-33-8

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

B

(S)‑3‑carbamoylmethyl‑5‑methylhexanoic acid
181289-34-9

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

Conditions
ConditionsYield
With (R)-1-phenyl-ethyl-amine Resolution of racemate;
(3S)-3-(2-methoxy-2-oxoethyl)-5-methylhexanoic acid
181289-25-8

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

A

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
181289-33-8

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

B

(S)‑3‑carbamoylmethyl‑5‑methylhexanoic acid
181289-34-9

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

Conditions
ConditionsYield
Stage #1: (3S)-3-(2-methoxy-2-oxoethyl)-5-methylhexanoic acid With ammonia In water at 20℃; for 92h;
Stage #2: With hydrogenchloride In water pH=3;
5-methyl-3-carboxymethylhexanoic acid
75143-89-4

5-methyl-3-carboxymethylhexanoic acid

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
181289-33-8

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: urea / 12 h / 130 - 135 °C
1.2: 60 - 90 °C
2.1: chloroform / 0.5 h / 50 - 55 °C
3.1: hydrogenchloride / water / 1.47 h / 20 - 25 °C
View Scheme
Multi-step reaction with 4 steps
1.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere
2.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C
2.2: pH 2
3.1: acetone / water / 80 °C
4.1: ammonia / water / 5 h / 80 °C
4.2: 0 °C / pH 1
View Scheme
Multi-step reaction with 4 steps
1.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere
2.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C
2.2: pH 2
3.1: chloroform; ethanol / 0.75 h / 60 - 63 °C
4.1: ammonia / water / 5 h / 80 °C
4.2: 0 °C / pH 1
View Scheme
(S)‑3‑carbamoylmethyl‑5‑methylhexanoic acid
181289-34-9

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

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
181289-33-8

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid / toluene / Reflux
1.2: 25 - 65 °C
1.3: 1.5 h / 10 - 15 °C
2.1: chloroform / 0.5 h / 50 - 55 °C
3.1: hydrogenchloride / water / 1.47 h / 20 - 25 °C
View Scheme
isovaleraldehyde
590-86-3

isovaleraldehyde

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
181289-33-8

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

Conditions
ConditionsYield
Multi-step reaction with 4 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
3.1: chloroform / 0.5 h / 50 - 55 °C
4.1: hydrogenchloride / water / 1.47 h / 20 - 25 °C
View Scheme
Multi-step reaction with 7 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
6.1: acetone / water / 80 °C
7.1: ammonia / water / 5 h / 80 °C
7.2: 0 °C / pH 1
View Scheme
Multi-step reaction with 7 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
6.1: chloroform; ethanol / 0.75 h / 60 - 63 °C
7.1: ammonia / water / 5 h / 80 °C
7.2: 0 °C / pH 1
View Scheme
3-isobutylglutaric anhydride
185815-59-2

3-isobutylglutaric anhydride

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
181289-33-8

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C
1.2: pH 2
2.1: acetone / water / 80 °C
3.1: ammonia / water / 5 h / 80 °C
3.2: 0 °C / pH 1
View Scheme
Multi-step reaction with 3 steps
1.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C
1.2: pH 2
2.1: chloroform; ethanol / 0.75 h / 60 - 63 °C
3.1: ammonia / water / 5 h / 80 °C
3.2: 0 °C / pH 1
View Scheme
Multi-step reaction with 4 steps
1.1: 1,4-diaza-bicyclo[2.2.2]octane / tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere
2.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere
2.2: 2 h / -20 °C
2.3: 0 °C
3.1: acetone / water / 80 °C
4.1: ammonia / water / 5 h / 80 °C
4.2: 0 °C / pH 1
View Scheme
Multi-step reaction with 4 steps
1.1: 1,4-diaza-bicyclo[2.2.2]octane / tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere
2.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere
2.2: 2 h / -20 °C
2.3: 0 °C
3.1: chloroform; ethanol / 0.75 h / 60 - 63 °C
4.1: ammonia / water / 5 h / 80 °C
4.2: 0 °C / pH 1
View Scheme
Multi-step reaction with 2 steps
1: dmap / toluene / -20 - -10 °C / Industrial scale
2: hydrogen; palladium 10% on activated carbon / methanol / 12 h / 30 °C / 7500.75 Torr / Autoclave; Industrial scale
View Scheme
diethyl 2-(3-methylbutylidene)malonate
51615-30-6

diethyl 2-(3-methylbutylidene)malonate

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
181289-33-8

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

Conditions
ConditionsYield
Multi-step reaction with 6 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
5.1: acetone / water / 80 °C
6.1: ammonia / water / 5 h / 80 °C
6.2: 0 °C / pH 1
View Scheme
Multi-step reaction with 6 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
5.1: chloroform; ethanol / 0.75 h / 60 - 63 °C
6.1: ammonia / water / 5 h / 80 °C
6.2: 0 °C / pH 1
View Scheme
Multi-step reaction with 7 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
6.1: chloroform; ethanol / 0.75 h / 60 - 63 °C
7.1: ammonia / water / 5 h / 80 °C
7.2: 0 °C / pH 1
View Scheme
Multi-step reaction with 7 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
6.1: acetone / water / 80 °C
7.1: ammonia / water / 5 h / 80 °C
7.2: 0 °C / pH 1
View Scheme
2-isobutyl-propane-1,1,3,3-tetracarboxylic acid tetraethyl ester
102710-09-8

2-isobutyl-propane-1,1,3,3-tetracarboxylic acid tetraethyl ester

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
181289-33-8

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hydrogen bromide / water / 72 h / 100 °C
2.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere
3.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C
3.2: pH 2
4.1: acetone / water / 80 °C
5.1: ammonia / water / 5 h / 80 °C
5.2: 0 °C / pH 1
View Scheme
Multi-step reaction with 5 steps
1.1: hydrogen bromide / water / 72 h / 100 °C
2.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere
3.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C
3.2: pH 2
4.1: chloroform; ethanol / 0.75 h / 60 - 63 °C
5.1: ammonia / water / 5 h / 80 °C
5.2: 0 °C / pH 1
View Scheme
Multi-step reaction with 6 steps
1.1: hydrogen bromide / water / 72 h / 100 °C
2.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere
3.1: 1,4-diaza-bicyclo[2.2.2]octane / tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere
4.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere
4.2: 2 h / -20 °C
4.3: 0 °C
5.1: chloroform; ethanol / 0.75 h / 60 - 63 °C
6.1: ammonia / water / 5 h / 80 °C
6.2: 0 °C / pH 1
View Scheme
Multi-step reaction with 6 steps
1.1: hydrogen bromide / water / 72 h / 100 °C
2.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere
3.1: 1,4-diaza-bicyclo[2.2.2]octane / tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere
4.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere
4.2: 2 h / -20 °C
4.3: 0 °C
5.1: acetone / water / 80 °C
6.1: ammonia / water / 5 h / 80 °C
6.2: 0 °C / pH 1
View Scheme
(1'SR,3 SR)-1-(1'-napthyl)ethyl-3-(carboxylomethyl)-5-methylhexanoate
1385049-46-6

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

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
181289-33-8

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere
1.2: 2 h / -20 °C
1.3: 0 °C
2.1: acetone / water / 80 °C
3.1: ammonia / water / 5 h / 80 °C
3.2: 0 °C / pH 1
View Scheme
Multi-step reaction with 3 steps
1.1: chloroformic acid ethyl ester; triethylamine / acetone / -20 °C / Inert atmosphere
1.2: 2 h / -20 °C
1.3: 0 °C
2.1: chloroform; ethanol / 0.75 h / 60 - 63 °C
3.1: ammonia / water / 5 h / 80 °C
3.2: 0 °C / pH 1
View Scheme
R-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid quinine salt

R-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid quinine salt

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
181289-33-8

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

Conditions
ConditionsYield
Stage #1: R-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid quinine salt With ammonia In water at 80℃; for 5h;
Stage #2: With hydrogenchloride In water at 0℃; pH=1;
1,5-diallyl 3-isobutylpentanedioate
1403953-90-1

1,5-diallyl 3-isobutylpentanedioate

(3R)‐3‐(carbamoylmethyl)‐5‐methylhexanoic acid
181289-33-8

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: immobilized lipase B from Candida antartica; sodium hydroxide / aq. phosphate buffer / 15.6 h / 25 °C / pH 7 / Enzymatic reaction
2.1: magnesium nitride / methanol / 16 h / 20 - 80 °C
2.2: pH 3 - 4
View Scheme

(R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid 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

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