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

Base Information

• Chemical Name: (3S)-3-[4-(2-[¹⁸F]fluoroethoxy)phenyl]-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid
• CAS No.: 1423134-50-2
• Molecular Formula: C₂₅H₃₆FN₃O₅
• Molecular Weight: 476.578

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

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

There total 4 articles about (3S)-3-[4-(2-[¹⁸F]fluoroethoxy)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:

tert-butyl 4-{3-[(3R)-3-({3-methoxy-1-[4-(2-{[(4-methylphenyl)sulfonyl]oxy}ethoxy)phenyl]-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate → (3S)-3-[4-(2-[18F]fluoroethoxy)phenyl]-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid (1423134-50-2)

Guidance literature:

tert-butyl 4-{3-[(3R)-3-({3-methoxy-1-[4-(2-{[(4-methylphenyl)sulfonyl]oxy}ethoxy)phenyl]-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate; With K₁₈F*C₁₈H₃₆N₂O₆; In acetonitrile; at 100 ℃; for 0.166667h; Sealed tube;

With sodium hydroxide; at 25 ℃; for 0.166667h;

With hydrogenchloride; at 100 ℃; for 0.166667h;

Reference yield:

3-amino-3-(4-hydroxyphenyl)propionic acid (6049-54-3) → (3S)-3-[4-(2-[18F]fluoroethoxy)phenyl]-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid (1423134-50-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: thionyl chloride / 20 h / 0 - 20 °C

2.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 0 - 20 °C

3.1: caesium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C

4.1: K₁₈F*C₁₈H₃₆N₂O₆ / acetonitrile / 0.17 h / 100 °C / Sealed tube

4.2: Zorbax BOnus RP 5μm C18-HL (9.4 X 250 nm) / 0.17 h / 25 °C

4.3: 0.17 h / 100 °C

With thionyl chloride; K₁₈F*C₁₈H₃₆N₂O₆; caesium carbonate; N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; acetonitrile;

Reference yield:

3-amino-3-(4-hydroxyphenyl)propionic acid methyl ester (166954-93-4) → (3S)-3-[4-(2-[18F]fluoroethoxy)phenyl]-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid (1423134-50-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: HATU; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 0 - 20 °C

2.1: caesium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C

3.1: K₁₈F*C₁₈H₃₆N₂O₆ / acetonitrile / 0.17 h / 100 °C / Sealed tube

3.2: Zorbax BOnus RP 5μm C18-HL (9.4 X 250 nm) / 0.17 h / 25 °C

3.3: 0.17 h / 100 °C

With K₁₈F*C₁₈H₃₆N₂O₆; caesium carbonate; N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

3-amino-3-(4-hydroxyphenyl)propionic acid methyl ester

3-amino-3-(4-hydroxyphenyl)propionic acid

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

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