H2N-PEG2-tBu CAS 756525-95-8

Introduction：Basic information about H2N-PEG2-tBu CAS 756525-95-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

H2N-PEG2-tBu Basic information

• Product Name: H2N-PEG2-tBu
• Synonyms: H2N-PEG2-tBu;tert-Butyl 9-AMino-4,7-dioxanonanoate (H2N-PEG2-tBu) tert-butyl 9-AMino-4,7-dioxanonanoate;3-[2-(2-Aminoethoxy)ethoxy]propanoic acid 1,1-dimethylethyl ester;H2N-PEG2-CH2CH2COOtBu;Amino-PEG2-t-butyl ester;H₂N-PEG₂-CH₂CH₂COO^tBu;Amino-PEG2-acid -t-Butyl ester;tert-Butyl 3-(2-(2-aminoethoxy)ethoxy)propanoate
• CAS: 756525-95-8
• MF: C11H23NO4
• MW: 233.3
• Product Categories: PEG-COOtBu;ADCs Linkers;PROTAC Linker;PROTAC;peg
• Mol File: 756525-95-8.mol

H2N-PEG2-tBu Chemical Properties

• Boiling point: 313.7±22.0 °C(Predicted)
• density: 1.014±0.06 g/cm3(Predicted)
• storage temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• pka: 8.74±0.10(Predicted)
• form: Liquid
• color: Colorless to light yellow
• InChI: InChI=1S/C11H23NO4/c1-11(2,3)16-10(13)4-6-14-8-9-15-7-5-12/h4-9,12H2,1-3H3
• InChIKey: XIVHGTLMLORWEP-UHFFFAOYSA-N
• SMILES: C(OC(C)(C)C)(=O)CCOCCOCCN

Safety Information

• HS Code: 2922500090

H2N-PEG2-tBu Usage And Synthesis

Description

Amino-PEG2-t-butyl ester is a PEG linker containing an amino group with a t-butyl protected carboxyl group (Boc).The amino group is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. The t-butyl protected carboxyl group can be deprotected under acidic conditions.

Uses

3-[2-(2-Aminoethoxy)Ethoxy]Propanoic Acid 1,1-Dimethylethyl Ester is used as reactant in the synthesis of self-localizing ligands that control spatial location of proteins in living cells.

Synthesis

1629676-61-4

756525-95-8

General procedure for the synthesis of tert-butyl 9-amino-4,7-dioxanonanoate from the compound (CAS: 1629676-61-4): 5% Pd/C (JM US 2.14 g) was added to a solution of dibenzylamine 27 (35.0 g, 85 mmol) in methanol (420 mL), and the mixture was placed in an Atlantis reactor and subjected to a hydrogenation reaction at 40 °C and 15 psi hydrogen pressure for the hydrogenation reaction. After 2 h of reaction, the catalyst was removed by filtration and the filtrate was concentrated to yield 18.90 g (96% yield) of amine 7 as a turbid oil, which was used directly in the next step of the reaction without further purification.IR (ATR cells): 2977, 2868, 1727, 1456, 1393, 1367, 1254, 1157, 1113, 847, 755, 589, 564, 547, 536 cm^-1. ^1H NMR (400 MHz, CDCl3): δ = 1.30 (s, 9H), 2.36 (t, J = 6.43 Hz, 2H), 2.71 (t, J = 5.19 Hz, 2H), 3.36 (t, J = 5.19 Hz, 2H), 3.43-3.50 (m, 4H) , 3.57 (t, J = 6.64 Hz, 2H). ^13C NMR (100 MHz, CDCl3): δ = 28.18, 36.36, 41.92, 66.98, 70.32, 70.44, 73.58, 80.52, 170.92. HRMS (ESI): m/z [M + H]^+ Calculated value for C11H24NO4: 234.16998; measured value: 234.17009.

IC 50

PEGs; Alkyl/ether; Non-cleavable Linker

References

[1] Synthesis (Germany), 2014, vol. 46, # 10, p. 1399 - 1406
[2] Patent: WO2016/59622, 2016, A2. Location in patent: Page/Page column 104
[3] Patent: WO2017/46658, 2017, A1. Location in patent: Page/Page column 144
[4] Patent: WO2018/86139, 2018, A1. Location in patent: Page/Page column 152

H2N-PEG2-tBu Preparation Products And Raw materials

• Raw materials: Propanoic acid, 3-[2-[2-[bis(phenylmethyl)amino]ethoxy]ethoxy]-, 1,1-dimethylethyl ester-->Azido-PEG2-t-butyl ester-->Palladium-->Methanol-->Activated carbon-->Hydrogen
• Preparation Products: Azido-PEG2-acid