(S)-(-)-2-Hydroxy-3,3-dimethylbutyric acid

Base Information

• Chemical Name: (S)-(-)-2-Hydroxy-3,3-dimethylbutyric acid
• CAS No.: 21641-92-9
• Molecular Formula: C6H12O3
• Molecular Weight: 132.159
• Hs Code.: 29181998
• European Community (EC) Number: 624-886-9
• Nikkaji Number: J955.960D
• Mol file: 21641-92-9.mol

Synonyms:21641-92-9;(S)-2-hydroxy-3,3-dimethylbutanoic acid;(S)-(-)-2-Hydroxy-3,3-dimethylbutyric acid;(2S)-2-hydroxy-3,3-dimethylbutanoic acid;(S)-(-)-2-Hydroxy-tert-butylacetic acid;851866-86-9;Butanoic acid, 2-hydroxy-3,3-dimethyl-, (2S)-;MFCD00192212;(S)-2-hydroxy-3,3-dimethyl-butyric acid;(R)-TRIMETHYLLACTIC ACID;(2S)-2-hydroxy-3,3-dimethyl-butanoic acid;SCHEMBL640168;FWVNWTNCNWRCOU-SCSAIBSYSA-N;AMY13579;WAA64192;AKOS016846181;CS-W005786;DS-5093;(S)-2-hydroxy-3,3-dimethylbutanoicacid;(s)-2-hydroxy-3,3-dimethylbutyric acid;(s)-3,3-dimethyl-2-hydroxybutyric acid;BP-12914;(S)-2-hydroxy-3,3-dimethyl butyric acid;(S)-2-hydroxy-3,3-dimethyl butanoic acid;(2S)-3,3-dimethyl-2-oxidanyl-butanoic acid;EN300-1132065;A815568;J-014202;(S)-(-)-2-Hydroxy-3,3-dimethylbutyric acid, 97%

Chemical Property of (S)-(-)-2-Hydroxy-3,3-dimethylbutyric acid

Chemical Property:

• Vapor Pressure: 0.006mmHg at 25°C
• Melting Point: 48-50oC
• Refractive Index: 1.459
• Boiling Point: 242.4oCat760mmHg
• PKA: 3.91±0.27(Predicted)
• Flash Point: 114.6oC
• PSA: 60.36000
• Density: 1.1g/cm³
• LogP: -0.85670
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 132.078644241
• Heavy Atom Count: 9
• Complexity: 112

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-2-Hydroxy-3,3-dimethylbutanoicacid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(C(=O)O)O
• Isomeric SMILES: CC(C)(C)[C@@H](C(=O)O)O
• Uses: Building block for chiral tert-butyl substituted α-lactams, diols, and α-hydroxyketones.

Technology Process of (S)-(-)-2-Hydroxy-3,3-dimethylbutyric acid

There total 14 articles about (S)-(-)-2-Hydroxy-3,3-dimethylbutyric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

L-tert-Leucine (20859-02-3) → (S)-2-hydroxy-3,3-dimethylbutanoic acid (21641-92-9,851866-86-9)

Guidance literature:

With sodium nitrite; In water; 1.) room temp., 24 h 2.) 60 degC, 30 min;

DOI:10.1002/jlac.198219821105

Reference yield: 77.0%

trimethylpyruvic acid (815-17-8) → (S)-2-hydroxy-3,3-dimethylbutanoic acid (21641-92-9,851866-86-9)

Guidance literature:

With sodium tetrahydroborate; esterification with (S)-phenylethylamine and hydrolysis;

DOI:10.1021/ja00222a026

Reference yield:

trimethylpyruvic acid (815-17-8) → (2R)-3,3-Dimethyl-2-hydroxybutyric acid (22146-57-2,851866-86-9) + (S)-2-hydroxy-3,3-dimethylbutanoic acid (21641-92-9,851866-86-9)

Guidance literature:

With [iridium(dihydride)(chloride)((3,5-(tBu)2-C₆H₃)2P)(C₁₇H₁₀)NHCHC₅H₃N(CH₃)]; potassium tert-butylate; hydrogen; In butan-1-ol; at 25 - 30 ℃; for 21h; under 11400.8 Torr; Reagent/catalyst; Overall yield = 92 %; enantioselective reaction; Autoclave;

DOI:10.1039/c4cc07643e

upstream raw materials:

3,3-dimethyl-butan-2-one

L-tert-Leucine

trimethylpyruvic acid

1,1-dibromo-3,3-dimethylbutan-2-one

Downstream raw materials:

(S)-3-hydroxy-4,4-dimethylpentan-2-one

benzyl 2-hydroxy-3,3-dimethylbutanoate

(2S)-1-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-3,3-dimethyl-1-oxobutan-2-ol

7-(4-chlorophenyl)-2-((S)-2-hydroxy-3,3-dimethylbutyryl)-1,3,4,5,10,11a-hexahydro-2H-2,4a,10-triazadibenzo[a,d]cyclohepten-11-one

Refernces

• 1、 Horn, Alexander,Kazmaier, Uli. "Stereoselective Modification of N-(α-Hydroxyacyl)-glycinesters via Palladium-Catalyzed Allylic Alkylation". supporting information. p. 4595 - 4599. Retrieved 2019/06/27.
• 2、 -. "Asymmetric hydrogenation reaction of alpha-ketoacids compound". Paragraph 0037; 0044. . Retrieved 2016/10/10.