(3R,5S)-3-Hydroxy-4,4-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; compound with 2,2,4a,7,7-pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine

Base Information

• Chemical Name: (3R,5S)-3-Hydroxy-4,4-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; compound with 2,2,4a,7,7-pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine
• CAS No.: 80403-49-2
• Molecular Formula: C₉H₁₃NO₄*C₁₃H₂₄N₂
• Molecular Weight: 407.553

Synonyms:

Chemical Property of (3R,5S)-3-Hydroxy-4,4-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; compound with 2,2,4a,7,7-pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (3R,5S)-3-Hydroxy-4,4-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; compound with 2,2,4a,7,7-pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine

There total 5 articles about (3R,5S)-3-Hydroxy-4,4-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; compound with 2,2,4a,7,7-pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine 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: 95.0%

(2S,3S,5R)-3-Hydroxy-4,4-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (77150-73-3,80434-19-1,81872-03-9) + 1,2,3,4,4a,5,6,7-octahydro-2,2,4a,7,7-pentametyl-1,8-naphthyridene (69340-58-5,308280-56-0,1212823-64-7) → (3R,5S)-3-Hydroxy-4,4-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; compound with 2,2,4a,7,7-pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine (80403-49-2)

Guidance literature:

palladium on activated charcoal; In tetrahydrofuran; for 1h; Ambient temperature; hydrogenolysis;

DOI:10.1016/S0040-4039(01)81973-0

Reference yield:

(2S,5R)-4,4-Dimethyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (80403-45-8) → (3R,5S)-3-Hydroxy-4,4-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; compound with 2,2,4a,7,7-pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine (80403-49-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / NaBH₄ / tetrahydrofuran; ethanol / -60 - -50 °C

2: 95 percent / 10percent Pd-C / tetrahydrofuran / 1 h / Ambient temperature; hydrogenolysis

With sodium tetrahydroborate; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1016/S0040-4039(01)81973-0

Reference yield:

[2-(1-Chlorocarbonyl-1-methyl-ethyl)-4-oxo-azetidin-1-yl]-acetic acid benzyl ester (80403-44-7) → (3R,5S)-3-Hydroxy-4,4-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; compound with 2,2,4a,7,7-pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine (80403-49-2)

Guidance literature:

Multi-step reaction with 3 steps

1: LiN(TMS)2 / tetrahydrofuran / 0.25 h / -78 °C

2: 98 percent / NaBH₄ / tetrahydrofuran; ethanol / -60 - -50 °C

3: 95 percent / 10percent Pd-C / tetrahydrofuran / 1 h / Ambient temperature; hydrogenolysis

With sodium tetrahydroborate; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1016/S0040-4039(01)81973-0

upstream raw materials:

(2S,3S,5R)-3-Hydroxy-4,4-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

1,2,3,4,4a,5,6,7-octahydro-2,2,4a,7,7-pentametyl-1,8-naphthyridene

(2S,5R)-4,4-Dimethyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

[2-(1-Chlorocarbonyl-1-methyl-ethyl)-4-oxo-azetidin-1-yl]-acetic acid benzyl ester

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