tert-Butyl glycinate

Base Information

• Chemical Name: tert-Butyl glycinate
• CAS No.: 6456-74-2
• Molecular Formula: C6H13NO2
• Molecular Weight: 131.175
• Hs Code.: 29224999
• Mol file: 6456-74-2.mol

Synonyms:Glycine,tert-butyl ester (6CI,7CI,8CI);1,1-Dimethylethyl glycinate;Aminoacetic acidtert-butyl ester;Aminoacetic acid tert-butyl ester;[(tert-Butoxycarbonyl)methyl]amine;tert-Butyl 2-aminoacetate;tert-Butylaminoacetate;tert-Butyl glycinate;

Chemical Property of tert-Butyl glycinate

Chemical Property:

• Appearance/Colour: White crystalline powder/Colorless Clear Liquid
• Melting Point: 148-150 °C (decomp)
• Refractive Index: 1.4240
• Boiling Point: 145.7 °C at 760 mmHg
• PKA: 7.36±0.29(Predicted)
• Flash Point: 20.7 °C
• PSA: 52.32000
• Density: 0.973 g/cm³
• LogP: 0.98710
• Storage Temp.: Store at +2°C to +8°C.
• Sensitive.: Air Sensitive
• Water Solubility.: Miscible with acetone and methanol. Slightly miscible with ehtanol. Immiscible with water.

Purity/Quality:

98% ^*data from raw suppliers

tert-Butyl2-Aminoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/38:Irritating to eyes and skin.
• Hazard Codes: R36/38:Irritating to eyes and skin.
• Statements: 36/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Glycine tert-butyl ester is used in the preparation of Schiff base by reacting with benzophenone. The resultant Schiff base undergoes asymmetric alkylation with arylmethyl bromides in the presence of O-allyl-N-(9-anthracenylmethyl)cinchonidinium bromide as chiral phase transfer catalyst to give guanidine-containing pentacyclic compound.

Technology Process of tert-Butyl glycinate

There total 22 articles about tert-Butyl glycinate 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%

tert-butyl N-(benzyloxycarbonyl)glycinate (16881-32-6) → Glycine tert-butyl ester (6456-74-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1002/ejoc.200300410

Reference yield: 91.0%

glycine tert-butyl ester hydrochloride (27532-96-3) → Glycine tert-butyl ester (6456-74-2)

Guidance literature:

With ammonia; In dichloromethane; for 0.333333h; Schlenk technique; Inert atmosphere;

DOI:10.1002/ejoc.202100259

Reference yield: 90.0%

bromoacetic acid tert-butyl ester (5292-43-3) → Glycine tert-butyl ester (6456-74-2)

Guidance literature:

With ammonia; In diethyl ether; 1.) -40 deg C, 2 h, 2.) RT, overnight;

upstream raw materials:

tert-butyl 2-azidoacetate

tert-butyl N-(benzyloxycarbonyl)glycinate

tert-butyl 2-(1,3-dioxoisoindolin-2-yl)acetate

tert-butyl N-(trifluoroacetyl)glycinate

Downstream raw materials:

tert-butyl 2-(2-(((benzyloxy)carbonyl)amino)propanamido)acetate

Z-Phe-Gly-OtBu

N-Z-Ile-Gly-OC(CH₃)3

Z-Tyr(-Bzl)-Gly-OtBu

Refernces

• 1、 Albat, Dominik,Neud?rfl, J?rg-Martin,Schmalz, Hans-Günther. "A General Stereocontrolled Synthesis of Opines through Asymmetric Pd-Catalyzed N-Allylation of Amino Acid Esters". supporting information. p. 2099 - 2102. Retrieved 2021/07/22.
• 2、 Begam, Hasina Mamataj,Jana, Ranjan,Manna, Kartic,Samanta, Krishanu. "Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids". supporting information. p. 7443 - 7449. Retrieved 2020/10/09.