(1R,4R,5S)-1-((1S)-1-Hydroxy-2-methylpropyl)-4-propyl-6-oxa-2-azabicyclo(3.2.0)heptane-3,7-dione

Base Information

• Chemical Name: (1R,4R,5S)-1-((1S)-1-Hydroxy-2-methylpropyl)-4-propyl-6-oxa-2-azabicyclo(3.2.0)heptane-3,7-dione
• CAS No.: 211866-70-5
• Molecular Formula: C12H19NO4
• UNII: 35Y6H8EGE9
• Nikkaji Number: J1.222.949F
• Wikidata: Q27123574
• Metabolomics Workbench ID: 58363
• Mol file: 211866-70-5.mol

Synonyms:MLN-519;PS 519;PS-519;PS519

Chemical Property of (1R,4R,5S)-1-((1S)-1-Hydroxy-2-methylpropyl)-4-propyl-6-oxa-2-azabicyclo(3.2.0)heptane-3,7-dione

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 241.13140809
• Heavy Atom Count: 17
• Complexity: 354

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCC1C2C(C(=O)O2)(NC1=O)C(C(C)C)O
• Isomeric SMILES: CCC[C@@H]1[C@H]2[C@](C(=O)O2)(NC1=O)[C@H](C(C)C)O

Technology Process of (1R,4R,5S)-1-((1S)-1-Hydroxy-2-methylpropyl)-4-propyl-6-oxa-2-azabicyclo(3.2.0)heptane-3,7-dione

There total 16 articles about (1R,4R,5S)-1-((1S)-1-Hydroxy-2-methylpropyl)-4-propyl-6-oxa-2-azabicyclo(3.2.0)heptane-3,7-dione 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%

3S-hydroxy-2R-(1S-hydroxy-2-methylpropyl)-4R-n-propyl-5-oxopyrrolidine-2-carboxylic acid (220805-59-4) → [1R-[1S,4R,5S]]-1-(1-hydroxy-2-methylpropyl)-4-n-propyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione (211866-70-5)

Guidance literature:

With Isopropenyl chloroformate; triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

DOI:10.1021/ja991175f

Reference yield:

methyl (2E)-4-methylpent-2-enoate (20515-15-5) → [1R-[1S,4R,5S]]-1-(1-hydroxy-2-methylpropyl)-4-n-propyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione (211866-70-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 60 percent / K₂OsO₂(OH)4; hydroquinine 1,4-phthalazinediyl diether; aq. N-methylmorpholine N-oxide / 2-methyl-propan-2-ol / 49 h / 20 °C

2.1: BF₃*OEt₂ / CH₂Cl₂ / 1.83 h / 20 °C

3.1: acetyl bromide / CH₂Cl₂ / 2.5 h / 20 °C

4.1: 85 percent / sodium azide / dimethylsulfoxide / 11 h / 20 °C

5.1: H₂; 20 percent Pd(OH)2/C; HCl / methanol; dioxane / 8 h / 20 °C

5.2: 89 percent / p-TsOH*H₂O / toluene / 2.75 h / Heating

6.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexane / 0.5 h / -76.5 °C

6.2: dimethylaluminum chloride / tetrahydrofuran; hexane / 0.67 h / -76.5 °C

6.3: tetrahydrofuran; hexane / 1.08 h / -81.5 - -20 °C

7.1: 79 percent / H₂; 20 percent Pd(OH)2/C / methanol; acetic acid / 75 h / 20 °C / 2844.31 Torr

8.1: 100 percent / aq. NaOH / 34 h / 4 °C

9.1: 75 percent / triethylamine; isopropenyl chloroformate / tetrahydrofuran / 1 h / 0 - 20 °C

With hydrogenchloride; palladium dihydroxide; sodium hydroxide; sodium azide; Hydroquinone 1,4-phthalazinediyl diether; potassium dioxotetrahydroxoosmate(VI); Acetyl bromide; Isopropenyl chloroformate; boron trifluoride diethyl etherate; hydrogen; 4-methylmorpholine N-oxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; acetic acid; dimethyl sulfoxide; tert-butyl alcohol; 1.1: dihydroxylation / 2.1: Condensation / 3.1: Ring cleavage / 4.1: azidation / 5.1: Hydrogenation / 5.2: Cyclization / 6.1: Metallation / 6.2: Substitution / 6.3: Condensation / 7.1: Hydrogenolysis / 8.1: Hydrolysis / 9.1: lactonization;

DOI:10.1021/ja991175f

Reference yield:

n-valeryl chloride (638-29-9) → [1R-[1S,4R,5S]]-1-(1-hydroxy-2-methylpropyl)-4-n-propyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione (211866-70-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

1.2: tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C

2.1: TiCl₄ / CH₂Cl₂ / 0.17 h / 4 °C

2.2: diisopropylethylamine / CH₂Cl₂ / 1 h / 4 °C

2.3: 85 percent / CH₂Cl₂ / 6 h / 0 - 4 °C

3.1: 90 percent / aq. H₂O₂; LiOH / tetrahydrofuran / 48 h / 4 °C

4.1: 98 percent / 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium*BF₄; diisopropylethylamine / acetonitrile / 2 h / 0 - 4 °C

5.1: H₂; 10 percent Pd(OH)2/C / methanol / 48 h / 20 °C / 760 Torr

6.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

7.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexane / 0.5 h / -76.5 °C

7.2: dimethylaluminum chloride / tetrahydrofuran; hexane / 0.67 h / -76.5 °C

7.3: tetrahydrofuran; hexane / 1.08 h / -81.5 - -20 °C

8.1: 79 percent / H₂; 20 percent Pd(OH)2/C / methanol; acetic acid / 75 h / 20 °C / 2844.31 Torr

9.1: 100 percent / aq. NaOH / 34 h / 4 °C

10.1: 75 percent / triethylamine; isopropenyl chloroformate / tetrahydrofuran / 1 h / 0 - 20 °C

With palladium dihydroxide; lithium hydroxide; sodium hydroxide; n-butyllithium; Isopropenyl chloroformate; hydrogen; dihydrogen peroxide; titanium tetrachloride; Dess-Martin periodane; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; acetic acid; acetonitrile; 1.1: Metallation / 1.2: Acylation / 2.1: complexation / 2.2: enolization / 2.3: benzyloxymethylation / 3.1: Hydrolysis / 4.1: Condensation / 5.1: Hydrogenation / 6.1: Oxidation / 7.1: Metallation / 7.2: Substitution / 7.3: Condensation / 8.1: Hydrogenolysis / 9.1: Hydrolysis / 10.1: lactonization;

DOI:10.1021/ja991175f

upstream raw materials:

3S-hydroxy-2R-(1S-hydroxy-2-methylpropyl)-4R-n-propyl-5-oxopyrrolidine-2-carboxylic acid

methyl (2E)-4-methylpent-2-enoate

n-valeryl chloride

(4R,5S)-5-isopropyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester

Refernces