(6S,7R,10S)-7-Isobutyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-6,10-dicarboxylic acid 6-(benzyloxy-amide) 10-methylamide

Base Information

• Chemical Name: (6S,7R,10S)-7-Isobutyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-6,10-dicarboxylic acid 6-(benzyloxy-amide) 10-methylamide
• CAS No.: 191409-07-1
• Molecular Formula: C₂₈H₃₇N₃O₅
• Molecular Weight: 495.619

Synonyms:(6S,7R,10S)-7-Isobutyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-6,10-dicarboxylic acid 6-(benzyloxy-amide) 10-methylamide

Chemical Property of (6S,7R,10S)-7-Isobutyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-6,10-dicarboxylic acid 6-(benzyloxy-amide) 10-methylamide

Chemical Property:

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Technology Process of (6S,7R,10S)-7-Isobutyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-6,10-dicarboxylic acid 6-(benzyloxy-amide) 10-methylamide

There total 15 articles about (6S,7R,10S)-7-Isobutyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-6,10-dicarboxylic acid 6-(benzyloxy-amide) 10-methylamide 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: 60.0%

N-benzyloxyamine (622-33-3) + (6S,7R,10S)-7-Isobutyl-10-methylcarbamoyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-triene-6-carboxylic acid (206555-17-1) → (6S,7R,10S)-7-Isobutyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-triene-6,10-dicarboxylic acid 6-(benzyloxy-amide) 10-methylamide (191409-07-1)

Guidance literature:

With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;

DOI:10.1021/jm970849z

Reference yield:

Benzyl 3S-(3-bromopropyl)-3-t-butoxycarbonyl-2(R)-isobutylpropanoate (191406-76-5) → (6S,7R,10S)-7-Isobutyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-triene-6,10-dicarboxylic acid 6-(benzyloxy-amide) 10-methylamide (191409-07-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / H₂ / Pd/C / methanol / 3 h

2: 75 percent / NMM; TBTU / dimethylformamide / 2 h / 20 °C

3: 74 percent / Cs₂CO₃ / dimethylformamide; dimethylsulfoxide / 0.5 h / 80 °C

4: 99 percent / TFA / 1 h / 20 °C

5: 81 percent / NMM; HATU / dimethylformamide / 20 - 60 °C

6: 99 percent / aq. LiOH / tetrahydrofuran / 2 h / 20 °C

7: NMM; TBTU / dimethylformamide / 18.25 h / 20 - 80 °C

With 4-methyl-morpholine; lithium hydroxide; hydrogen; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm010127e

Reference yield:

4-benzyl 1-tert-butyl (2S,3R)-2-(3-hydroxypropyl)-3-isobutylbutanedioate (191406-75-4) → (6S,7R,10S)-7-Isobutyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-triene-6,10-dicarboxylic acid 6-(benzyloxy-amide) 10-methylamide (191409-07-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 65 percent / CBr₄; PPh₃; imidazole / CH₂Cl₂ / 3.33 h / 0 - 20 °C

2: 99 percent / H₂ / Pd/C / methanol / 3 h

3: 75 percent / NMM; TBTU / dimethylformamide / 2 h / 20 °C

4: 74 percent / Cs₂CO₃ / dimethylformamide; dimethylsulfoxide / 0.5 h / 80 °C

5: 99 percent / TFA / 1 h / 20 °C

6: 81 percent / NMM; HATU / dimethylformamide / 20 - 60 °C

7: 99 percent / aq. LiOH / tetrahydrofuran / 2 h / 20 °C

8: NMM; TBTU / dimethylformamide / 18.25 h / 20 - 80 °C

With 4-methyl-morpholine; 1H-imidazole; lithium hydroxide; carbon tetrabromide; hydrogen; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triphenylphosphine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm010127e

upstream raw materials:

N-benzyloxyamine

(6S,7R,10S)-7-Isobutyl-10-methylcarbamoyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-6-carboxylic acid

methylamine hydrochloride

6-benzyloxycarbamoyl-7-isobutyl-9-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-10-carboxylic acid

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