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Structure

N-Boc-4-pentyne-1-amine

CAS
151978-50-6
Catalog Number
ACM151978506
Category
Other Products; Main Products
Molecular Weight
183.25
Molecular Formula
C10H17NO2

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Specification

Synonyms
N-Boc-4-pentyne-1-amine, N-Boc-5-amino-1-pentyne, tert-Butyl (4-pentynyl)carbamate, 151978-50-6, 4-Pentynylcarbamic acid tert-butyl ester, ACMC-1BYWG, CTK8C5498, AB76351, TERT-BUTYL PENT-4-YNYLCARBAMATE, TERT-BUTYL N-(PENT-4-YN-1-YL)CARBAMATE
IUPAC Name
tert-butyl N-pent-4-ynylcarbamate
Canonical SMILES
CC(C)(C)OC(=O)NCCCC#C
InChI Key
JTPJJKZSKWNWKK-UHFFFAOYSA-N
Appearance
Liquid
Exact Mass
183.12600
H-Bond Acceptor
2
H-Bond Donor
1

N-Boc-4-Pentyne-1-Amine Used for the Synthesis of PROTAC BET Degraders

Zhou, Bing, et al. Journal of medicinal chemistry, 2018, 61(2), 462-481.

This work designed a new type of BET protein PROTAC small molecule degraders. Among them, N-Boc-4-pentyne-1-amine can be used as a linker for the synthesis of PROTAC BET degrader 20.
Synthesis procedure of PROTAC BET degrader 20
· In a round-bottom flask, compound 53 (1.0 equivalent) and N-Boc-4-pentyne-1-amine (2.0 equivalent) were dissolved in 0.2 equivalent CuI and 0.1 equivalent Pd(PPh3)2Cl2 solutions in 10 mL of DMF. It was emptied of nitrogen, then refilled three times. Added trimethylamine (5.0 mL) and purified, refilled with nitrogen again. Reaction was stirred in argon at 70 °C for 3 hours. Once the mixture was chilled to room temperature, it was filtered through Celite, and the residue was flash column chromatographed into compound 54a, which was a slightly yellow solid.
· Then 60 mg of 10% Pd/C was added to a solution of compound 54a (1.0 equivalent) in 10 mL of ethanol on nitrogen. It filtered and refilled the solution three times with hydrogen, and shook at room temperature for 12 hours. Filtration, with solvent filtered off, crude residue 55a. This was dispersed in 4.0 mL of DCM and 2.0 mL of TFA and stirred for 1 hour at room temperature. Purification by preparative HPLC yielded compound 56a as an oil of colorless. Lastly, HATU (1.4 equivalents), DIPEA (3.0 equivalents) and 56a (1.4 equivalents) were dissolved one by one in a stirred solution of compound 34 (1.0 equivalent) in 2.0 mL of DMF. Two hours of room temperature stirring purified the end product 20, isolated as a slightly yellow liquid.

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