tert-butyl 6-oxo-6-[(3aS,7aS)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]hexylcarbamate

Base Information

Chemical Name:tert-butyl 6-oxo-6-[(3aS,7aS)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]hexylcarbamate
CAS No.:1605314-20-2
Molecular Formula:C₁₈H₃₀N₂O₅
Molecular Weight:354.447
Hs Code.:

Synonyms:tert-butyl 6-oxo-6-[(3aS,7aS)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]hexylcarbamate

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Chemical Property of tert-butyl 6-oxo-6-[(3aS,7aS)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]hexylcarbamate

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Technology Process of tert-butyl 6-oxo-6-[(3aS,7aS)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]hexylcarbamate

There total 1 articles about tert-butyl 6-oxo-6-[(3aS,7aS)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]hexylcarbamate 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:

: 6404-29-1
6-(tert-butoxycarbonylamino)hexanoic acid

: 1605314-20-2
tert-butyl 6-oxo-6-[(3aS,7aS)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]hexylcarbamate

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylamine / tetrahydrofuran / 0.25 h / -15 °C

1.2: 2 h / -15 °C

2.1: lithium chloride / tetrahydrofuran / 18 h / 20 °C

With triethylamine; lithium chloride; In tetrahydrofuran;
DOI:10.1002/ejoc.201301834

Reference yield: 53.0%

: 1605314-20-2
tert-butyl 6-oxo-6-[(3aS,7aS)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]hexylcarbamate

: 5437-45-6
Benzyl bromoacetate

: 1605314-22-4
(R)-benzyl 7-(tert-butoxycarbonylamino)-3-[(3aS,7aS)-2-oxooctahydro-benzo[d]oxazole-3-carbonyl]heptanoate

Guidance literature:: tert-butyl 6-oxo-6-[(3aS,7aS)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]hexylcarbamate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1.25h;

Benzyl bromoacetate; In tetrahydrofuran; at -78 ℃; for 5h; diastereoselective reaction;
DOI:10.1002/ejoc.201301834

Reference yield:

: 1605314-20-2
tert-butyl 6-oxo-6-[(3aS,7aS)-2-oxohexahydrobenzo[d]oxazol-3(2H)-yl]hexylcarbamate

: 1605314-26-8
benzyl {(R)-6-tert-butoxycarbonylamino-2-[(3aS,7aS)-2-oxooctahydrobenzo[d]oxazole-3-carbonyl]-hexyl}carbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.25 h / -78 °C

1.2: 5 h / -78 °C

2.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 24 h / 760.05 Torr

3.1: triethylamine; diphenyl phosphoryl azide / 3 h / 20 °C / Reflux

With diphenyl phosphoryl azide; palladium 10% on activated carbon; hydrogen; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; ethyl acetate; 3.1: |Curtius Rearrangement;
DOI:10.1002/ejoc.201301834