tert-butyl ([1,1'-biphenyl]-4-ylmethyl)((1S,3R)-3-(pent-4-enoyl)cyclopentyl)carbamate

Base Information

• Chemical Name: tert-butyl ([1,1'-biphenyl]-4-ylmethyl)((1S,3R)-3-(pent-4-enoyl)cyclopentyl)carbamate
• CAS No.: 1431568-41-0
• Molecular Formula: C₂₈H₃₅NO₃
• Molecular Weight: 433.591
• Mol file: 1431568-41-0.mol

Synonyms:tert-butyl ([1,1'-biphenyl]-4-ylmethyl)((1S,3R)-3-(pent-4-enoyl)cyclopentyl)carbamate

Chemical Property of tert-butyl ([1,1'-biphenyl]-4-ylmethyl)((1S,3R)-3-(pent-4-enoyl)cyclopentyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl ([1,1'-biphenyl]-4-ylmethyl)((1S,3R)-3-(pent-4-enoyl)cyclopentyl)carbamate

There total 6 articles about tert-butyl ([1,1'-biphenyl]-4-ylmethyl)((1S,3R)-3-(pent-4-enoyl)cyclopentyl)carbamate 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: 94.0%

tert-butyl-[1,1'-biphenyl]-4-ylmethyl-{(1S,3R)-3-(methoxy(methyl)carbamoyl)-cyclopentyl}-carbamate (1431568-40-9) + 4-but-1-enylmagnesium bromide (7103-09-5) → tert-butyl ([1,1'-biphenyl]-4-ylmethyl)((1S,3R)-3-(pent-4-enoyl)cyclopentyl)carbamate (1431568-41-0)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

Reference yield:

(1R,3S)-3-((biphenyl-4-ylmethyl)(tert-butoxycarbonyl)amino)cyclopentane carboxylic acid (1431568-39-6) → tert-butyl ([1,1'-biphenyl]-4-ylmethyl)((1S,3R)-3-(pent-4-enoyl)cyclopentyl)carbamate (1431568-41-0)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

2: tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane;

Reference yield:

(1R,3S)-3-aminocyclopentanecarboxylic acid (71830-08-5) → tert-butyl ([1,1'-biphenyl]-4-ylmethyl)((1S,3R)-3-(pent-4-enoyl)cyclopentyl)carbamate (1431568-41-0)

Guidance literature:

Multi-step reaction with 5 steps

1: acetic acid / methanol / 1 h

2: sodium tris(acetoxy)borohydride / methanol / 4.17 h / 20 °C

3: sodium hydrogencarbonate / ethyl acetate; water / 20 °C

4: dmap; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

5: tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With dmap; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate;

upstream raw materials:

(1R,3S)-3-((biphenyl-4-ylmethyl)(tert-butoxycarbonyl)amino)cyclopentane carboxylic acid

tert-butyl-[1,1'-biphenyl]-4-ylmethyl-{(1S,3R)-3-(methoxy(methyl)carbamoyl)-cyclopentyl}-carbamate

4-but-1-enylmagnesium bromide

(1R,3S)-3-(biphenyl-4-ylmethylamino)cyclopentanecarboxylic acid

Downstream raw materials:

tert-butyl (1S,3S)-3-{(2-acetamido-1-(tert-butylamino)-1-oxo-hex-5-en-2-yl)cyclopentyl-[1,1'-biphenyl]-4-ylmethyl}-carbamate

tert-butyl (1S,3S)-3-{(2-acetamido-1-(tert-butylamino)-1-oxo-hex-5-en-2-yl)cyclopentyl-[1,1'-biphenyl]-4-ylmethyl}-carbamate