(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

Base Information

• Chemical Name: (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
• CAS No.: 120363-40-8
• Molecular Formula: C₂₆H₂₆N₂O₄
• Molecular Weight: 430.503

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 18 articles about (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 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: 68.0%

3-[4-(3-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-ethyl}-phenoxy)-phenyl]-propionic acid; hydrochloride (120363-43-1) → (S)-12-<(4-Hydroxyphenyl)methyl>-11,14-dioxo-2-oxa-10,13-diazatricyclo<15.2.2.13,7>docosa-3,5,7(22),17,19,20-hexaene (120363-40-8)

Guidance literature:

With diphenylphosphoranyl azide; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 0 ℃; for 72h;

DOI:10.1021/jo00272a003

Reference yield: 49.0%

(S)-2-(3-{4-[3-(2-Amino-ethyl)-phenoxy]-phenyl}-propionylamino)-3-(4-hydroxy-phenyl)-propionic acid pentafluorophenyl ester; hydrochloride (120363-35-1) → (S)-12-<(4-Hydroxyphenyl)methyl>-11,14-dioxo-2-oxa-10,13-diazatricyclo<15.2.2.13,7>docosa-3,5,7(22),17,19,20-hexaene (120363-40-8)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 90 ℃; for 1h;

DOI:10.1021/jo00311a019 DOI:10.1021/jo00272a003

Reference yield:

3-(3-hydroxyphenyl)-propanoic acid (621-54-5) → (S)-12-<(4-Hydroxyphenyl)methyl>-11,14-dioxo-2-oxa-10,13-diazatricyclo<15.2.2.13,7>docosa-3,5,7(22),17,19,20-hexaene (120363-40-8)

Guidance literature:

Multi-step reaction with 10 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

10: 68 percent / diphenylphosphorazidate, NaHCO₃ / dimethylformamide / 72 h / 0 °C

With hydrogenchloride; lithium hydroxide; diphenyl phosphoryl azide; diphenyl-phosphinic acid; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 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

upstream raw materials:

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

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

3-(3-hydroxyphenyl)-propanoic acid

L-Tyr-OMe

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