tert-Butyl 3-aminopropanoate

Name: tert-Butyl 3-aminopropanoate
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 15231-41-1

Cat No.: BP-500070

Purity: 95% 4.5

tert-Butyl 3-aminopropanoate is a protected amino acid derivative featuring a three-carbon aliphatic linker terminating in a primary amine, with the carboxyl group masked as a tert-butyl ester. This structural arrangement makes it a practical building block for PROTAC linker synthesis, because the ester protection enables controlled coupling chemistry while preserving the amine for subsequent functionalization. In targeted protein degradation workflows, such linkers are engineered to tune the spatial relationship between the ligand that recruits the E3 ligase and the ligand that binds the target protein, thereby influencing ternary complex formation and degradation efficiency. Researchers commonly use amino-protected propyl units to introduce flexible, hydrophilic segments that can be further converted into amide or carbamate linkages during final PROTAC assembly. As a versatile intermediate, it supports systematic structure–activity studies aimed at optimizing linker length, flexibility, and attachment points for robust, reproducible degrader design.

Structure of 15231-41-1

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Category

PROTAC Linker

Molecular Formula

C7H15NO2

Molecular Weight

145.20

* For research and manufacturing use only. Not for human or clinical use.

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Purity

95%

Storage

4°C, protect from light; In solvent, -80°C, 6 months; -20°C, 1 month (protect from light)

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Room temperature in continental US; may vary elsewhere.

IUPACName

tert-butyl 3-aminopropanoate

Synonyms

tert-butyl3-aminopropanoate; beta-alaninetert-butylester; 3-Aminopropionicacidtert-butylester; 3-amino-propionicacidtert-butylester; N-Bocethylamine

InChI Key

ZJXHVYSDMUKUCA-UHFFFAOYSA-N

InChI

InChI=1S/C7H15NO2/c1-7(2,3)10-6(9)4-5-8/h4-5,8H2,1-3H3

SMILES

CC(C)(C)OC(=O)CCN

1.Syntheses and bioactivities of substituted 9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrones. Unusual reactivities with amines.

Hua DH1, Tamura M, Huang X, Stephany HA, Helfrich BA, Perchellet EM, Sperfslage BJ, Perchellet JP, Jiang S, Kyle DE, Chiang PK. J Org Chem. 2002 May 3;67(9):2907-12.

A number of substituted 9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrones have been synthesized and their anticancer and antimalarial activities evaluated. A one-pot synthesis of 2,5,8-trimethoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4-dione (4) was achieved by heating a mixture of 1,4-dimethoxyanthracene, methoxyhydroquinone, silver oxide, and zinc iodide in toluene. Regioselective bromination of 4 and 2-methoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone (7) with N-bromosuccinimide provided 2-bromo-3,5,8-trimethoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4-dione and 2-bromo-3-methoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone (1), respectively. The reactions of 1 with aliphatic primary amines and secondary amines, respectively, produced different products, a result most likely attributed to the different basicities (or nucleophilicities) and steric effects of the two kinds of amines. The structure of the displacement product, 2-bromo-3-[2-(tert-butoxycarbonyl)ethylamino]-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone, from the reaction of 1 with tert-butyl 3-aminopropanoate was unequivocally determined by a single-crystal X-ray analysis.

This PROTAC linker building block, tert-Butyl 3-aminopropanoate, provides a protected primary amine suitable for constructing amide- and urea-forming connections that underpin targeted protein degradation scaffolds. Its tert-butyl ester functionality offers practical stability during multi-step synthesis, while the amino terminus enables controlled coupling to warheads or E3 ligase ligands. The combination of orthogonal reactivity and synthetic versatility makes it a valuable intermediate for assembling PROTACs, with detailed structural and reaction considerations provided below.

Structure: The molecule contains a tert-butyl ester protecting group on a three-carbon amino acid side chain, featuring an aliphatic primary amine and an ester linkage. Its structure includes C–N and C–O single bonds with an aliphatic backbone, yielding a polarizable, non-aromatic linker suitable for stepwise functionalization.

Reactivity: Use the protected ester to maintain compatibility with coupling steps that require amine availability. The primary amine can participate in standard amide coupling or related bond-forming reactions using activated carboxylic acid derivatives. Typical conditions involve carbodiimide or acyl-activated chemistries in anhydrous organic solvents, while ester deprotection is commonly achieved under acid-mediated conditions to reveal the carboxylate for subsequent PROTAC assembly.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂