methyl (6S,7R,10S)-6-{[(benzyloxy)amino]carbonyl}-7-isobutyl-8-oxo-2-oxa-9-azabicyclo[10.2.2]hexadeca-1⁽¹⁴⁾,12,15-triene-10-carboxylate

Base Information

• Chemical Name: methyl (6S,7R,10S)-6-{[(benzyloxy)amino]carbonyl}-7-isobutyl-8-oxo-2-oxa-9-azabicyclo[10.2.2]hexadeca-1⁽¹⁴⁾,12,15-triene-10-carboxylate
• CAS No.: 191406-81-2
• Molecular Formula: C₂₈H₃₆N₂O₆
• Molecular Weight: 496.604

Synonyms:methyl (6S,7R,10S)-6-{[(benzyloxy)amino]carbonyl}-7-isobutyl-8-oxo-2-oxa-9-azabicyclo[10.2.2]hexadeca-1⁽¹⁴⁾,12,15-triene-10-carboxylate

Chemical Property of methyl (6S,7R,10S)-6-{[(benzyloxy)amino]carbonyl}-7-isobutyl-8-oxo-2-oxa-9-azabicyclo[10.2.2]hexadeca-1⁽¹⁴⁾,12,15-triene-10-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of methyl (6S,7R,10S)-6-{[(benzyloxy)amino]carbonyl}-7-isobutyl-8-oxo-2-oxa-9-azabicyclo[10.2.2]hexadeca-1⁽¹⁴⁾,12,15-triene-10-carboxylate

There total 9 articles about methyl (6S,7R,10S)-6-{[(benzyloxy)amino]carbonyl}-7-isobutyl-8-oxo-2-oxa-9-azabicyclo[10.2.2]hexadeca-1⁽¹⁴⁾,12,15-triene-10-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: 81.0%

O-benzylhydoxylamine hydrochloride (2687-43-6) + (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 10-methyl ester (191406-80-1) → methyl (6S,7R,10S)-6-{[(benzyloxy)amino]carbonyl}-7-isobutyl-8-oxo-2-oxa-9-azabicyclo[10.2.2]hexadeca-1(14),12,15-triene-10-carboxylate (191406-81-2)

Guidance literature:

With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 - 60 ℃;

DOI:10.1021/jm010127e

Reference yield:

Benzyl 3S-(3-bromopropyl)-3-t-butoxycarbonyl-2(R)-isobutylpropanoate (191406-76-5) → methyl (6S,7R,10S)-6-{[(benzyloxy)amino]carbonyl}-7-isobutyl-8-oxo-2-oxa-9-azabicyclo[10.2.2]hexadeca-1(14),12,15-triene-10-carboxylate (191406-81-2)

Guidance literature:

Multi-step reaction with 5 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

With 4-methyl-morpholine; 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 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) → methyl (6S,7R,10S)-6-{[(benzyloxy)amino]carbonyl}-7-isobutyl-8-oxo-2-oxa-9-azabicyclo[10.2.2]hexadeca-1(14),12,15-triene-10-carboxylate (191406-81-2)

Guidance literature:

Multi-step reaction with 6 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

With 4-methyl-morpholine; 1H-imidazole; 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 methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm010127e

upstream raw materials:

O-benzylhydoxylamine hydrochloride

(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 10-methyl ester

L-tyrosine methyl ester HCl

(2R,3S)-6-bromo-3-(tert-butoxycarbonyl)-2-isobutylhexanoic acid

Downstream raw materials:

(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-{[(S)-2-(4-methoxy-phenyl)-1-methylcarbamoyl-ethyl]-amide}

(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-[((S)-2-tert-butoxy-1-methylcarbamoyl-ethyl)-amide]

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