3-[4-(3-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-ethyl}-phenoxy)-phenyl]-propionic acid; hydrochloride

Base Information

• Chemical Name: 3-[4-(3-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-ethyl}-phenoxy)-phenyl]-propionic acid; hydrochloride
• CAS No.: 120363-43-1
• Molecular Formula: C₂₆H₂₈N₂O₅*ClH
• Molecular Weight: 484.98

Synonyms:3-[4-(3-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-ethyl}-phenoxy)-phenyl]-propionic acid; hydrochloride

Chemical Property of 3-[4-(3-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-ethyl}-phenoxy)-phenyl]-propionic acid; hydrochloride

Chemical Property:

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Technology Process of 3-[4-(3-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-ethyl}-phenoxy)-phenyl]-propionic acid; hydrochloride

There total 11 articles about 3-[4-(3-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-ethyl}-phenoxy)-phenyl]-propionic acid; hydrochloride 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:

3-(3-hydroxyphenyl)-propanoic acid (621-54-5) → 3-[4-(3-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-ethyl}-phenoxy)-phenyl]-propionic acid; hydrochloride (120363-43-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / NaH, n-Bu₄NI / dimethylformamide / 10 h / 25 °C

2: Et₃N, DPPA / 8 h / 85 °C

3: H₂ / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C / 2280 Torr

5: 97 percent / H₂ / 10percent Pd/C / methanol / 3 h / 25 °C / 2280 Torr

6: 3.0M HCl / ethyl acetate / 25 °C

7: EDCI / dimethylformamide / 25 °C

8: LiOH, H₂O / methanol; tetrahydrofuran / 25 °C

9: 3.0M HCl / ethyl acetate

With hydrogenchloride; lithium hydroxide; diphenyl-phosphinic acid; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00311a019

Reference yield:

3-(3-(benzyloxy)phenyl)propanoic acid (57668-34-5) → 3-[4-(3-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-ethyl}-phenoxy)-phenyl]-propionic acid; hydrochloride (120363-43-1)

Guidance literature:

Multi-step reaction with 8 steps

1: Et₃N, DPPA / 8 h / 85 °C

2: H₂ / 10percent Pd/C / tetrahydrofuran / 6 h / 25 °C / 2280 Torr

4: 97 percent / H₂ / 10percent Pd/C / methanol / 3 h / 25 °C / 2280 Torr

5: 3.0M HCl / ethyl acetate / 25 °C

6: EDCI / dimethylformamide / 25 °C

7: LiOH, H₂O / methanol; tetrahydrofuran / 25 °C

8: 3.0M HCl / ethyl acetate

With hydrogenchloride; lithium hydroxide; diphenyl-phosphinic acid; water; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00311a019

Reference yield:

trans-3-(4-iodophenyl)-2-propenoic acid ethyl ester (161634-73-7) → 3-[4-(3-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-ethyl}-phenoxy)-phenyl]-propionic acid; hydrochloride (120363-43-1)

Guidance literature:

Multi-step reaction with 6 steps

2: 97 percent / H₂ / 10percent Pd/C / methanol / 3 h / 25 °C / 2280 Torr

3: 3.0M HCl / ethyl acetate / 25 °C

4: EDCI / dimethylformamide / 25 °C

5: LiOH, H₂O / methanol; tetrahydrofuran / 25 °C

6: 3.0M HCl / ethyl acetate

With hydrogenchloride; lithium hydroxide; water; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00311a019

upstream raw materials:

3-(3-hydroxyphenyl)-propanoic acid

3-(3-(benzyloxy)phenyl)propanoic acid

Boc-Tyr-OH

trans-3-(4-iodophenyl)-2-propenoic acid ethyl ester

Downstream raw materials:

(S)-12-<(4-Hydroxyphenyl)methyl>-11,14-dioxo-2-oxa-10,13-diazatricyclo<15.2.2.1^3,7>docosa-3,5,7(22),17,19,20-hexaene

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