benzyl (S)-2-benzyl-3-oxo-3-[(3aR,7aR)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]propylcarbamate

Base Information

Chemical Name:benzyl (S)-2-benzyl-3-oxo-3-[(3aR,7aR)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]propylcarbamate
CAS No.:1605314-18-8
Molecular Formula:C₂₅H₂₈N₂O₅
Molecular Weight:436.508
Hs Code.:

Synonyms:benzyl (S)-2-benzyl-3-oxo-3-[(3aR,7aR)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]propylcarbamate

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Chemical Property of benzyl (S)-2-benzyl-3-oxo-3-[(3aR,7aR)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]propylcarbamate

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Technology Process of benzyl (S)-2-benzyl-3-oxo-3-[(3aR,7aR)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]propylcarbamate

There total 5 articles about benzyl (S)-2-benzyl-3-oxo-3-[(3aR,7aR)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]propylcarbamate 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: 75.0%

: 1605314-16-6
(S)-3-benzyl-4-oxo-4-[(3aR,7aR)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]butanoic acid

: 100-51-6,185532-71-2
benzyl alcohol

: 1605314-18-8
benzyl (S)-2-benzyl-3-oxo-3-[(3aR,7aR)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]propylcarbamate

Guidance literature:: With diphenyl phosphoryl azide; triethylamine; for 3h; Reflux;
DOI:10.1002/ejoc.201301834

Reference yield:

: 1605314-14-4
(S)-benzyl 3-benzyl-4-oxo-4-[(3aR,7aR)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]butanoate

: 1605314-18-8
benzyl (S)-2-benzyl-3-oxo-3-[(3aR,7aR)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]propylcarbamate

Guidance literature:: Multi-step reaction with 2 steps

1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 16 h / 760.05 Torr

2: triethylamine; diphenyl phosphoryl azide / 3 h / Reflux

With diphenyl phosphoryl azide; palladium 10% on activated carbon; hydrogen; triethylamine; In ethyl acetate; 2: |Curtius Rearrangement;
DOI:10.1002/ejoc.201301834

Reference yield:

: 189942-49-2
(4R,5R)-trans-hexahydrobenzoxazolidin-2-one

: 1605314-18-8
benzyl (S)-2-benzyl-3-oxo-3-[(3aR,7aR)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]propylcarbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -20 °C

1.2: 3.75 h / -20 - 20 °C

2.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -78 °C

2.2: 12 h / -78 °C

3.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 16 h / 760.05 Torr

4.1: triethylamine; diphenyl phosphoryl azide / 3 h / Reflux

With n-butyllithium; diphenyl phosphoryl azide; palladium 10% on activated carbon; hydrogen; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; ethyl acetate; 4.1: |Curtius Rearrangement;
DOI:10.1002/ejoc.201301834