(9S,12S)-12-[N-(tert-butyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene

Base Information

• Chemical Name: (9S,12S)-12-[N-(tert-butyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene
• CAS No.: 152429-89-5
• Molecular Formula: C₂₅H₃₀N₂O₇
• Molecular Weight: 470.522

Synonyms:(9S,12S)-12-[N-(tert-butyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene

Chemical Property of (9S,12S)-12-[N-(tert-butyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene

Chemical Property:

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Technology Process of (9S,12S)-12-[N-(tert-butyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-hexaene

There total 2 articles about (9S,12S)-12-[N-(tert-butyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7⁽¹⁹⁾,14,16,17-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: 72.0%

5-((S)-2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)-3-methoxy-3-oxopropyl)-2-methoxyphenylboronic acid (606139-98-4) → (9S,12S)-12-[N-(tert-butyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaene (152429-89-5) + (S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-(4-methoxy-phenyl)-propionic acid methyl ester

Guidance literature:

With copper diacetate; 4 Angstroem MS; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1016/S0040-4039(03)01390-X

Reference yield:

3-hydroxy-O-methyl-N-<4-iodo-N-<(1,1-dimethylethoxy)carbonyl>-L-phenylalanyl>-L-tyrosine methyl ester (1026064-05-0) → C21H20N2O6 + (S)-3-(3-Hydroxy-4-methoxy-phenyl)-2-[4-(4-iodo-benzyl)-2,5-dioxo-imidazolidin-1-yl]-propionic acid methyl ester + (9S,12S)-12-[N-(tert-butyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaene (152429-89-5)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction. Yields of byproduct given; 1.) pyridine, 0 deg C, 20 min, 2.) pyridine, 115 deg C, 9 h;

DOI:10.1021/ja00077a047

Reference yield:

(9S,12S)-12-[N-(tert-butyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.13,7]nonadeca-3,5,7(19),14,16,17-hexaene (152429-89-5) → N15,N29-desmethyl RA-VII (138571-36-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / HCl / ethyl acetate / 0.5 h / 25 °C

2: 87 percent / tetrahydrofuran / 2 h / 25 °C

3: 93 percent / aq. LiOH / tetrahydrofuran; methanol / 8 h / 25 °C

4: 100 percent / HCl / ethyl acetate / 1.) 0 deg C, 10 min, 2.) 25 deg C, 50 min

5: 80 percent / NaHCO₃, diphenylphosphoryl Azide / dimethylformamide / 48 h / 4 °C

With hydrogenchloride; lithium hydroxide; diphenylphosphoranyl azide; sodium hydrogencarbonate; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja00133a010

upstream raw materials:

3-hydroxy-O-methyl-N-<4-iodo-N-<(1,1-dimethylethoxy)carbonyl>-L-phenylalanyl>-L-tyrosine methyl ester

5-((S)-2-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanamido)-3-methoxy-3-oxopropyl)-2-methoxyphenylboronic acid

Downstream raw materials:

(9S,12S)-12-Amino-4-methoxy-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3,5,7⁽¹⁹⁾,14⁽¹⁸⁾,15-hexaene-9-carboxylic acid benzyl ester

(9S,12S)-12-tert-Butoxycarbonylamino-4-methoxy-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3,5,7⁽¹⁹⁾,14⁽¹⁸⁾,15-hexaene-9-carboxylic acid benzyl ester

(9S,12S)-12-{2-[2-(2-tert-Butoxycarbonylamino-acetylamino)-acetylamino]-acetylamino}-4-methoxy-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3,5,7⁽¹⁹⁾,14⁽¹⁸⁾,15-hexaene-9-carboxylic acid benzyl ester

(9S,12S)-12-(2-{2-[2-(2-tert-Butoxycarbonylamino-acetylamino)-acetylamino]-acetylamino}-acetylamino)-4-methoxy-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3,5,7⁽¹⁹⁾,14⁽¹⁸⁾,15-hexaene-9-carboxylic acid benzyl ester

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