(3S)-3-(3-{2-[2-(2-[¹⁸F]fluoroethoxy)ethoxy]ethoxy}phenyl)-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid

Base Information

• Chemical Name: (3S)-3-(3-{2-[2-(2-[¹⁸F]fluoroethoxy)ethoxy]ethoxy}phenyl)-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid
• CAS No.: 1423134-59-1
• Molecular Formula: C₂₉H₄₄FN₃O₇
• Molecular Weight: 564.684

Synonyms:(3S)-3-(3-{2-[2-(2-[¹⁸F]fluoroethoxy)ethoxy]ethoxy}phenyl)-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid

Chemical Property of (3S)-3-(3-{2-[2-(2-[¹⁸F]fluoroethoxy)ethoxy]ethoxy}phenyl)-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid

Chemical Property:

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Technology Process of (3S)-3-(3-{2-[2-(2-[¹⁸F]fluoroethoxy)ethoxy]ethoxy}phenyl)-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid

There total 10 articles about (3S)-3-(3-{2-[2-(2-[¹⁸F]fluoroethoxy)ethoxy]ethoxy}phenyl)-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid 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:

triethylene glycol di-(p-toluenesulfonate) (19249-03-7) → (3S)-3-(3-{2-[2-(2-[18F]fluoroethoxy)ethoxy]ethoxy}phenyl)-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid (1423134-59-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: [18F]KF-K₂₂₂ / acetonitrile / 0.17 h / 100 °C / Inert atmosphere; Sealed tube

2.1: sodium hydroxide / N,N-dimethyl-formamide / 0.02 h / 25 °C / Sealed tube

2.2: 0.5 h / 25 - 100 °C / Sealed tube

With sodium hydroxide; In N,N-dimethyl-formamide; acetonitrile;

Reference yield:

toluene-4-sulfonic acid 2-[2-(2-[18F]-fluoroethoxy)ethoxy]ethyl ester (1423135-40-3) + tert-butyl 4-{3-[(3R)-3-{[(1S)-1-(3-hydroxyphenyl)-3-methoxy-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate (1423134-77-3) → (3S)-3-(3-{2-[2-(2-[18F]fluoroethoxy)ethoxy]ethoxy}phenyl)-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid (1423134-59-1)

Guidance literature:

tert-butyl 4-{3-[(3R)-3-{[(1S)-1-(3-hydroxyphenyl)-3-methoxy-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate; With sodium hydroxide; In N,N-dimethyl-formamide; at 25 ℃; for 0.0166667h; Sealed tube;

toluene-4-sulfonic acid 2-[2-(2-[¹⁸F]-fluoroethoxy)ethoxy]ethyl ester; With hydrogenchloride; sodium hydroxide; In water; N,N-dimethyl-formamide; at 25 - 100 ℃; for 0.5h; Sealed tube;

Reference yield:

tert-butyl {[3-(benzyloxy)phenyl](phenylsulfonyl)methyl}carbamate (1423134-70-6) → (3S)-3-(3-{2-[2-(2-[18F]fluoroethoxy)ethoxy]ethoxy}phenyl)-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid (1423134-59-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: caesium carbonate; 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea / water; toluene / 144 h / -20 - 0 °C

2.1: formic acid / 20 h / 0 - 5 °C

3.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 0 °C

4.1: formic acid / 120 h / 20 °C

5.1: triethylamine / tetrahydrofuran / 4 h / 60 °C

6.1: triethylamine / dichloromethane / 2 h

7.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 16 h

8.1: sodium hydroxide / N,N-dimethyl-formamide / 0.02 h / 25 °C / Sealed tube

8.2: 0.5 h / 25 - 100 °C / Sealed tube

With formic acid; palladium 10% on activated carbon; hydrogen; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

upstream raw materials:

triethylene glycol di-(p-toluenesulfonate)

toluene-4-sulfonic acid 2-[2-(2-[¹⁸F]-fluoroethoxy)ethoxy]ethyl ester

tert-butyl 4-{3-[(3R)-3-{[(1S)-1-(3-hydroxyphenyl)-3-methoxy-3-oxopropyl]carbamoyl}piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate

tert-butyl {[3-(benzyloxy)phenyl](phenylsulfonyl)methyl}carbamate

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