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

Uses Sources

Product Name: (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid
CAS No.: 181289-33-8
Chemical Name: (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid
Synonyms: methylhexanoic acid;INTERMEDIATE OF PREGABALIN;(3R)-3-(2-AMino-2-oxoethyl)-5-Methylhexanoic Acid;(r)-(-)-3-(2-amino-2-oxoethyl)-5-methylhexanoic acid;PGL-S-CMH acid;Pregabalin Impurity 94;Pregabalin IMpurity III;Isobutyl-glutamonoamide;PREGABALINS INTERMEDIATES 03;Pregabalin Carbamoyl Impurity
CBNumber: CB2854928
Molecular Formula: C9H17NO3
Formula Weight: 187.24
MOL File: 181289-33-8.mol

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

Melting point:: 128-133°C
Boiling point:: 401.9±28.0 °C(Predicted)
Density: 1.080±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 4.68±0.10(Predicted)
color: White to Off-White
optical activity: -6.5461°(C=1.0048g/100ml DMF)
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
InChIKey: NPDKTSLVWGFPQG-SSDOTTSWSA-N
SMILES: C(O)(=O)C[C@@H](CC(N)=O)CC(C)C
CAS DataBase Reference: 181289-33-8(CAS DataBase Reference)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TRC

Product number: C175955
Product name: (R)-(-)-3-(Carbamoylmethyl)-5-methylhexanoicacid
Packaging: 5g
Price: $135
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FA140304
Product name: (R)-3-(2-Amino-2-oxoethyl)-5-methylhexanoic acid
Packaging: 10g
Price: $65
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FA140304
Product name: (R)-3-(2-Amino-2-oxoethyl)-5-methylhexanoic acid
Packaging: 25g
Price: $100
Updated: 2021/12/16

Matrix Scientific

Product number: 073067
Product name: R-(-)-3-(Carbamoylmethyl)-5-methylhexanoic acid
Purity: 95+%
Packaging: 25g
Price: $110
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: CCH0001191
Product name: (R)-(-)-3-(CARBAMOYMETHYL)-5-METHYLHEXANOIC ACID
Purity: 95.00%
Packaging: 1G
Price: $130.2
Updated: 2021/12/16

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(R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid Chemical Properties,Usage,Production

Uses

(R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid is a useful chemical intermediate for manufacturing of the anticonvulsant drug, Pregabalin^{1, 2}.

Sources

https://quod.lib.umich.edu/a/ark/5550190.0011.a22?rgn=main;view=fulltext
https://www.researchgate.net/publication/269660675_Synthesis_and_characterization_of_impurities_of_an_anticonvulsant_drug_Pregabalin

Chemical Properties

White Solid

Uses

An Impurity of the anti-convulsant (S)-Pregabalin (P704790).

Synthesis

1385049-51-3

181289-33-8

The general procedure for the synthesis of (R)-(-)-3-(aminocarbonylmethyl)-5-methylhexanoic acid from the compound (CAS:1385049-51-3) is as follows: Example 10f1: Synthesis of (R)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid 1. ammonia (116 ml) was added to the diastereomeric salt (14.5 g) and the mixture was heated to 80 °C at room temperature. 2. After maintaining the reaction at this temperature for 5 hours, the reaction mixture was cooled to room temperature. 3. The reaction mixture was extracted using dichloromethane (5 x 50 ml). 4. The aqueous layer was cooled to 0 °C and acidified to pH 1 with concentrated hydrochloric acid. 5. The acidified aqueous layer was extracted using hot ethyl acetate (5 x 50 ml). 6. All organic extracts were combined and concentrated under reduced pressure to give enantiomerically enriched amide I as a white solid. Yield: 8 g, 53% yield; HPLC purity: 99.39%.

References

[1] Patent: WO2012/93411, 2012, A2. Location in patent: Page/Page column 23

(R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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

Canada 2 China 335 India 38 Spain 1 United Kingdom 3 United States 15 Global 394

Hangzhou J&H Chemical Co., Ltd.

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View Lastest Price from (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid manufacturers

Shaanxi Dideu New Materials Co. Ltd

Product: (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid 181289-33-8
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 99.0%
Supply Ability: 10000KGS
Release date: 2025-05-26

WUHAN FORTUNA CHEMICAL CO., LTD

Product: (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid 181289-33-8
Price: US $0.00-0.00/Kg/Drum
Min. Order: 1KG
Purity: 99%min
Supply Ability: 1000kg
Release date: 2021-11-19

Hebei Chuanghai Biotechnology Co., Ltd

Product: (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid 181289-33-8
Price: US $10.00/KG
Min. Order: 100KG
Purity: 99%
Supply Ability: 100 mt
Release date: 2024-11-26

181289-33-8, (R)-(-)-3-Carbamoymethyl-5-methylhexanoic acidRelated Search:

EPA EC 2.3.2.2 ALTRENOGEST Hexamethylphosphoramide Ethyl 2-(Chlorosulfonyl)acetate Ethyl Hexanoate Phenylmethylsulfonyl fluoride Folic acid Glycine 3-(Aminomethyl)-5-methylhexanoic acid 3-(Aminomethyl)-5-methylhexanoic acid Dimethyl sulfone 6-Aminocaproic acid Tris(hydroxymethyl)aminomethane Citric acid Ascoric Acid 2-Hexenamide, 2-cyano-5-methyl- Hexanoic acid,3-(aminomethyl)-5-methyl-, (3R)-

(r)-(-)-3-(2-amino-2-oxoethyl)-5-methylhexanoic acid

(r)-(-)-3-carbamoymethyl-5-methylhexanoic acid

INTERMEDIATE OF PREGABALIN

(3R)-3-(2-AMino-2-oxoethyl)-5-Methylhexanoic Acid

(R)-3-(2-AMINO-2-OXOETHYL)-5-METHYLHEXANOIC ACID:99+%

3-CarbaMoyl Mehyl-5-Methyl Hexanoic Acid

Pregabalin IMpurity III

Hexanoic acid,3-(2-aMino-2-oxoethyl)-5-Methyl-,(3R)-

(R)-3-(2-AMino-2-oxoethyl)-5-Methylhexanoic acid (R)-3-(2-AMino-2-oxoethyl)-5-Methylhexanoic acid

Pregabalin Carbamoyl Impurity

(R)-(-)-3-Carbamoymethyl-5-methylhexanoic acid 181289-33-8

181289-33-8 (R)-(-)-3-(2-Amino-2-oxoethyl)-5-methylhexanoic acid

(±)-3-Carbamoylmethyl)-5-methyl hexanoic acid (CMH Acid)

methylhexanoic acid

Pregabalin Impurity III ((R)-(-)-3-(Carbamoylmethyl)-5-methylhexanoic acid)

Isobutyl-glutamonoamide

R-(-)-3-Carbamoylmethyl-5-hexanoic acid

(R)-(-)-3-carbamoy methyl)-5-methyl hexanoic acid(OR)

(R)-(-)-3-(CARBAMOYLMETHYL-5-METHYLMEXANOIC ACID

Pregabalin Impurity III (3-Carbamoymethyl-5-Methylhexanoic Acid)

(R)-3-(Carbamoylmethyl)-5-methylhex

Pregabalin 3-Carbamoylmethyl Impurity

PREGABALINS INTERMEDIATES 03

PGL-S-CMH acid

3-Carbamoylmethyl-5-methyl hexanoic acid (Recimic)

R-(-)-3-(Carbamoylmethyl)-5-methylhexanoicaci

?-(-)-3-(Carbamoyl methyl)-5-Methyl Haxanic Acid

R (-}3-CARSAMOYLMETIHYL-5-METHYLHEXANOIC ACID (RCMH)

3-(2-Amino-2-oxoethyl)-5-methyl-(3S)-hexanoicacid

3-(Carbamoyl)-5-Methyl Hexanoic Acid

R-(+)-3-(Carbamoylmethyl)-S- Methylhexanoic Acid

R-3-(Carbamoylmethyl)-5-Methylhexanoic Acid (Rcmh)

RCMH (R)-3-(2-Amino-2-oxoethyl)-5-methylhexanoic Acid

Isobutyl-glutamonoamide (R)-3-(2-amino-2-oxoethyl)-5-methylhexanoic acid

Pregablin Impurity (RCMH acid)

R-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid or R-Amide

Pregabalin Impurity 94

Isobutylglutarmonoamide (<i>R</i>-Isomer)

(r)-(-)-3-(2-amino-2-oxoethyl)-5-methylhexanoic acid, 98%min

3-(2-Amino-2-oxoethyl)-5-methyl-(3S)-hexanoicacid (Intermediate of Pregabalin)

181289-33-8

181289-33-6

Aliphatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals

intermidiate of Pregablin

Starting Raw Materials & Intermediates

181289-33-8