benzyl(10S,12S)-12-(acetylamino)-15,21-dioxo-8-oxa-3,14,17,20-tetraazatetracyclo[20.2.2.0²'⁷.0^10,14]hexacosa-1⁽²⁴⁾,2,4,6,22,25-hexaene-17-carboxylate

Base Information

• Chemical Name: benzyl(10S,12S)-12-(acetylamino)-15,21-dioxo-8-oxa-3,14,17,20-tetraazatetracyclo[20.2.2.0²'⁷.0^10,14]hexacosa-1⁽²⁴⁾,2,4,6,22,25-hexaene-17-carboxylate
• CAS No.: 1460303-78-9
• Molecular Formula: C₃₁H₃₃N₅O₆
• Molecular Weight: 571.633

Synonyms:benzyl(10S,12S)-12-(acetylamino)-15,21-dioxo-8-oxa-3,14,17,20-tetraazatetracyclo[20.2.2.0²'⁷.0^10,14]hexacosa-1⁽²⁴⁾,2,4,6,22,25-hexaene-17-carboxylate

Chemical Property of benzyl(10S,12S)-12-(acetylamino)-15,21-dioxo-8-oxa-3,14,17,20-tetraazatetracyclo[20.2.2.0²'⁷.0^10,14]hexacosa-1⁽²⁴⁾,2,4,6,22,25-hexaene-17-carboxylate

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Technology Process of benzyl(10S,12S)-12-(acetylamino)-15,21-dioxo-8-oxa-3,14,17,20-tetraazatetracyclo[20.2.2.0²'⁷.0^10,14]hexacosa-1⁽²⁴⁾,2,4,6,22,25-hexaene-17-carboxylate

There total 13 articles about benzyl(10S,12S)-12-(acetylamino)-15,21-dioxo-8-oxa-3,14,17,20-tetraazatetracyclo[20.2.2.0²'⁷.0^10,14]hexacosa-1⁽²⁴⁾,2,4,6,22,25-hexaene-17-carboxylate 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%

benzyl (10S,12S)-12-amino-15,21-dioxo-8-oxa-3,14,17,20-tetraazatetracyclo[20.2.2.02'7.010,14]hexacosa-1(24),2,4,6,22,25-hexaene-17-carboxylate dihydrochloride + acetyl chloride (75-36-5) → benzyl(10S,12S)-12-(acetylamino)-15,21-dioxo-8-oxa-3,14,17,20-tetraazatetracyclo[20.2.2.02'7.010,14]hexacosa-1(24),2,4,6,22,25-hexaene-17-carboxylate (1460303-78-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 2h;

Reference yield:

methyl 4-(3-hydroxypyridin-2-yl)benzoate (1261981-75-2) → benzyl(10S,12S)-12-(acetylamino)-15,21-dioxo-8-oxa-3,14,17,20-tetraazatetracyclo[20.2.2.02'7.010,14]hexacosa-1(24),2,4,6,22,25-hexaene-17-carboxylate (1460303-78-9)

Guidance literature:

Multi-step reaction with 8 steps

1: cyanomethylenetributyl-phosphorane / toluene / 1 h / 80 °C

2: lithium hydroxide; water / tetrahydrofuran; methanol / 16 h / 20 °C

3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h

4: lithium hydroxide; water / tetrahydrofuran; methanol / 16 h / 20 °C

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid / dichloromethane; ethyl acetate / 2 h / 20 °C

6: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 3 h

7: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C

8: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid; water; N-ethyl-N,N-diisopropylamine; HATU; cyanomethylenetributyl-phosphorane; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

Reference yield:

(9S,16S,19R)-16-benzyl-19,20-dimethyl-7-oxa-13,17,20,24-3,14,17,20-tetraazatetracyclo[20.2.2.02'7.010'14]hexacosa-1(24),2,4,6,22,25-hexaene-17-carboxylate (1460303-64-3) → benzyl(10S,12S)-12-(acetylamino)-15,21-dioxo-8-oxa-3,14,17,20-tetraazatetracyclo[20.2.2.02'7.010,14]hexacosa-1(24),2,4,6,22,25-hexaene-17-carboxylate (1460303-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 °C

With hydrogenchloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; dichloromethane;

upstream raw materials:

4-(3-hydroxypyridin-2-yl)benzoic acid

methyl 4-(3-hydroxypyridin-2-yl)benzoate

(9S,16S,19R)-16-benzyl-19,20-dimethyl-7-oxa-13,17,20,24-3,14,17,20-tetraazatetracyclo[20.2.2.0²'⁷.0¹⁰'¹⁴]hexacosa-1⁽²⁴⁾,2,4,6,22,25-hexaene-17-carboxylate

acetyl chloride

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