(R)-tert-Butyl 2-hydroxy-3-methylbutanoate

Base Information

• Chemical Name: (R)-tert-Butyl 2-hydroxy-3-methylbutanoate
• CAS No.: 4216-96-0
• Molecular Formula: C9H18O3
• Molecular Weight: 174.24
• Hs Code.: 2918199090
• European Community (EC) Number: 609-994-6
• DSSTox Substance ID: DTXSID00513569
• Nikkaji Number: J57.273J
• Wikidata: Q82373448
• Mol file: 4216-96-0.mol

Synonyms:4216-96-0;(R)-tert-Butyl 2-hydroxy-3-methylbutanoate;tert-Butyl (R)-2-hydroxy-3-methylbutyrate;tert-Butyl (2R)-2-hydroxy-3-methylbutanoate;(R)-tert-Butyl2-hydroxy-3-methylbutanoate;tert-Butyl (2R)-2-hydroxy-3-methyl-butanoate;SCHEMBL11855010;DTXSID00513569;AMY22239;CS-B0163;AKOS006285005;CS-13412;tert-butyl (R)-2-hydroxy-3-methylbutanoate;(R)-tert-butyl 2-hydroxy-3-methyl butanoate;A913591;J-502281

Chemical Property of (R)-tert-Butyl 2-hydroxy-3-methylbutanoate

Chemical Property:

• Vapor Pressure: 0.155mmHg at 25°C
• Melting Point: 28-30 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 189.5°C at 760 mmHg
• PKA: 12.94±0.20(Predicted)
• Flash Point: 63°C
• PSA: 46.53000
• Density: 0.974g/cm³
• LogP: 1.34500
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 174.125594432
• Heavy Atom Count: 12
• Complexity: 156

Purity/Quality:

98% ^*data from raw suppliers

(R)-tert-Butyl2-hydroxy-3-methylbutanoate 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)OC(C)(C)C)O
• Isomeric SMILES: CC(C)[C@H](C(=O)OC(C)(C)C)O

Technology Process of (R)-tert-Butyl 2-hydroxy-3-methylbutanoate

There total 7 articles about (R)-tert-Butyl 2-hydroxy-3-methylbutanoate 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: 92.0%

4-Nitro-benzoic acid (R)-1-tert-butoxycarbonyl-3-methyl-butyl ester (111505-51-2) → (-)-tert-butyl 2-hydroxy-3-methylbutanoate (4216-96-0)

Guidance literature:

With hydrazine hydrate; NaOH, pH= 10;

DOI:10.1016/S0040-4039(00)95997-5

Reference yield:

Propyl isocyanate (110-78-1) + α-hydroxy-isovaleric acid t-butyl ester (2528-17-8) → (-)-tert-butyl 3-methyl-2-propylaminocarbonyloxybutanoate + (+)-tert-butyl 3-methyl-2-propylaminocarbonyloxybutanoate (1349685-20-6) + (-)-tert-butyl 2-hydroxy-3-methylbutanoate (4216-96-0) + L-α-hydroxyisovaleric acid t-butyl ester (3519-30-0)

Guidance literature:

α-hydroxy-isovaleric acid t-butyl ester; With [Cu((S,S)-((CH₃)3CCHCH₂OCN)2C(CH₃)2)](CF₃SO₃)2; In dichloromethane; at 0 ℃; for 0.166667h; Inert atmosphere;

Propyl isocyanate; In dichloromethane; at 0 ℃; for 1h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/jo201940w

Reference yield:

(S)-2-Chloro-4-methyl-pentanoic acid tert-butyl ester (111505-47-6) → (-)-tert-butyl 2-hydroxy-3-methylbutanoate (4216-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 45 percent / dimethylformamide / 4 h / 80 °C

2: 92 percent / NH₂NH₂*H₂O / NaOH, pH= 10

With hydrazine hydrate; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)95997-5

upstream raw materials:

D-α-Acetoxy-isovaleriansaeure-tert-butylester

O-Benzyloxycarbonyl-D-α-hydroxy-isovaleriansaeure

isobutene

4-Nitro-benzoic acid (R)-1-tert-butoxycarbonyl-3-methyl-butyl ester

Downstream raw materials:

N-Benzyloxycarbonyl-N-methyl-D-Val-D-α-hydroxy-isovaleryl-N-methyl-D-Val-D-α-hydroxy-isovaleriansaeure-tert.-butylester

N-Benzyloxycarbonyl-N-methyl-L-Val-D-α-hydroxy-isovaleryl-N-methyl-L-Val-D-α-hydroxy-isovaleriansaeure-tert.-butylester

N-Benzyloxycarbonyl-N-methyl-L-Val-D-α-hydroxy-isovaleriansaeure

N-Benzyloxycarbonyl-N-methyl-D-Val-D-α-hydroxy-isovaleriansaeure