(9S,12S)-9-Benzyloxycarbonylamino-5-bromo-4-methoxy-17-nitro-10-oxo-2-oxa-11-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaene-12-carboxylic acid methyl ester

Base Information

• Chemical Name: (9S,12S)-9-Benzyloxycarbonylamino-5-bromo-4-methoxy-17-nitro-10-oxo-2-oxa-11-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaene-12-carboxylic acid methyl ester
• CAS No.: 412351-06-5
• Molecular Formula: C₂₈H₂₆BrN₃O₉
• Molecular Weight: 628.433

Synonyms:(9S,12S)-9-Benzyloxycarbonylamino-5-bromo-4-methoxy-17-nitro-10-oxo-2-oxa-11-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaene-12-carboxylic acid methyl ester

Chemical Property of (9S,12S)-9-Benzyloxycarbonylamino-5-bromo-4-methoxy-17-nitro-10-oxo-2-oxa-11-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaene-12-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (9S,12S)-9-Benzyloxycarbonylamino-5-bromo-4-methoxy-17-nitro-10-oxo-2-oxa-11-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaene-12-carboxylic acid methyl ester

There total 7 articles about (9S,12S)-9-Benzyloxycarbonylamino-5-bromo-4-methoxy-17-nitro-10-oxo-2-oxa-11-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,4,6,14⁽¹⁸⁾,15-hexaene-12-carboxylic acid methyl ester 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: 58.0%

(S)-2-[(S)-2-Benzyloxycarbonylamino-3-(3-bromo-5-hydroxy-4-methoxy-phenyl)-propionylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester (412351-05-4) → (9S,12S)-9-Benzyloxycarbonylamino-5-bromo-4-methoxy-17-nitro-10-oxo-2-oxa-11-aza-tricyclo[12.2.2.13,7]nonadeca-1(17),3(19),4,6,14(18),15-hexaene-12-carboxylic acid methyl ester (412351-06-5)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; at 25 ℃; for 18h;

DOI:10.1016/S0040-4039(01)02194-3

Reference yield:

L-3-(3-acetyl-4-hydroxyphenyl)-N-(benzyloxycarbonyl)alanine methyl ester (110774-03-3) → (9S,12S)-9-Benzyloxycarbonylamino-5-bromo-4-methoxy-17-nitro-10-oxo-2-oxa-11-aza-tricyclo[12.2.2.13,7]nonadeca-1(17),3(19),4,6,14(18),15-hexaene-12-carboxylic acid methyl ester (412351-06-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / N-bromosuccinimide / acetonitrile / 18 h / 25 °C

2: 94 percent / K₂CO₃ / dimethylformamide / 5 h / 25 °C

3: 61 percent / CF₃CO₃H / CH₂Cl₂ / 48 h / Heating

4: 88 percent / HCl / dioxane / 2 h / 25 °C

5: 68 percent / LiOH / tetrahydrofuran; H₂O / 1.5 h / 0 °C

6: 85 percent / EDCI; HOAt / dimethylformamide / 18 h / 25 °C

7: 58 percent / K₂CO₃ / dimethylsulfoxide / 18 h / 25 °C

With hydrogenchloride; lithium hydroxide; N-Bromosuccinimide; 1-hydroxy-7-aza-benzotriazole; trifluoroacetyl peroxide; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 3: Baeyer-Villiger oxidation;

DOI:10.1016/S0040-4039(01)02194-3

Reference yield:

(S)-2-Benzyloxycarbonylamino-3-(3-bromo-5-hydroxy-4-methoxy-phenyl)-propionic acid methyl ester (579469-95-7) → (9S,12S)-9-Benzyloxycarbonylamino-5-bromo-4-methoxy-17-nitro-10-oxo-2-oxa-11-aza-tricyclo[12.2.2.13,7]nonadeca-1(17),3(19),4,6,14(18),15-hexaene-12-carboxylic acid methyl ester (412351-06-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / LiOH / tetrahydrofuran; H₂O / 1.5 h / 0 °C

2: 85 percent / EDCI; HOAt / dimethylformamide / 18 h / 25 °C

3: 58 percent / K₂CO₃ / dimethylsulfoxide / 18 h / 25 °C

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)02194-3

upstream raw materials:

(S)-2-[(S)-2-Benzyloxycarbonylamino-3-(3-bromo-5-hydroxy-4-methoxy-phenyl)-propionylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

L-3-(3-acetyl-4-hydroxyphenyl)-N-(benzyloxycarbonyl)alanine methyl ester

(S)-2-Benzyloxycarbonylamino-3-(3-bromo-5-hydroxy-4-methoxy-phenyl)-propionic acid methyl ester

(S)-2-Benzyloxycarbonylamino-3-(3-bromo-5-hydroxy-4-methoxy-phenyl)-propionic acid

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