2-Pivalamidoacetic acid

Base Information

• Chemical Name: 2-Pivalamidoacetic acid
• CAS No.: 23891-96-5
• Molecular Formula: C7H13 N O3
• Molecular Weight: 159.185
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID40368979
• Nikkaji Number: J669.210I
• Wikidata: Q72471641
• Mol file: 23891-96-5.mol

Synonyms:N-pivaloylglycine

Chemical Property of 2-Pivalamidoacetic acid

Chemical Property:

• Vapor Pressure: 3.14E-06mmHg at 25°C
• Melting Point: 134-135 °C
• Boiling Point: 362.2°C at 760 mmHg
• PKA: 3.62±0.10(Predicted)
• Flash Point: 172.8°C
• PSA: 66.40000
• Density: 1.100±0.06 g/cm3(Predicted)
• LogP: 0.62420
• Storage Temp.: 2-8°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 159.08954328
• Heavy Atom Count: 11
• Complexity: 169

Purity/Quality:

98%min ^*data from raw suppliers

N-Pivaloylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(=O)NCC(=O)O
• Uses: N-Pivaloylglycine is used in the biological study between dogs and rats. In a high dose toxicity study of pivalic acid (PA), PA caused skeletal muscle disorder in dog, and a significant increase of pivaloyl carnitine (PC) was observed in canine muscle, but not in rat muscle.

Technology Process of 2-Pivalamidoacetic acid

There total 5 articles about 2-Pivalamidoacetic 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: 88.0%

succinimidyl 2,2-dimethylpropionate (42014-50-6) + glycine (56-40-6,18875-39-3,25718-94-9) → N-(2,2,2-trimethylacetyl)glycine (23891-96-5)

Guidance literature:

With sodium hydrogencarbonate; In water; at 20 ℃; for 4h;

Reference yield: 24.0%

pivaloyl chloride (3282-30-2) + glycine (56-40-6,18875-39-3,25718-94-9) → N-(2,2,2-trimethylacetyl)glycine (23891-96-5)

Guidance literature:

With sodium hydroxide; In water; Inert atmosphere; Schlenk technique;

DOI:10.1002/hlca.202100147

Reference yield: 12.0%

glycine ethyl ester hydrochloride (5680-79-5,883886-67-7) + pivaloyl chloride (3282-30-2) → N-(2,2,2-trimethylacetyl)glycine (23891-96-5)

Guidance literature:

glycine ethyl ester hydrochloride; pivaloyl chloride; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 16h; Inert atmosphere;

With methanol; sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b02543

upstream raw materials:

pivaloyl chloride

glycine

succinimidyl 2,2-dimethylpropionate

glycine ethyl ester hydrochloride

Downstream raw materials:

N-pivaloylaminomethyltriphenylphosphonium tetrafluoroborate

C₁₃H₁₉NOS

ethyl N-(2,2-dimethyl-1-oxopropyl)glycinate

(Z)-3-(3,4-dimethoxyphenyl)-N-methyl-2-pivaloylamino-2-propenamide

Refernces

• 1、 Chen, Jianzhong,Gridnev, Ilya D.,Hu, Yawen,Li, Bowen,Zhang, Wanbin,Zhang, Zhenfeng. "Nickel-Catalyzed Asymmetric Hydrogenation of 2-Amidoacrylates". supporting information. p. 5371 - 5375. Retrieved 2020/02/15.
• 2、 Maier, Norbert M.,Greco, Elisa,Petrovaj, Jan,Lindner, Wolf Gang. "Chromatographic enantiomer separation using 9-amino-9-(deoxy)-epiquinine- derived chiral selectors: Control of chiral recognition via introduction of additional stereogenic centers". . p. 454 - 463. Retrieved 2012/11/13.