(1S,4R,5R)-6-(2,4-Dimethoxy-benzyl)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (1S,4R,5R)-6-(2,4-Dimethoxy-benzyl)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester
• CAS No.: 269730-12-3
• Molecular Formula: C₃₀H₂₇N₃O₇
• Molecular Weight: 541.56
• Mol file: 269730-12-3.mol

Synonyms:(1S,4R,5R)-6-(2,4-Dimethoxy-benzyl)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Chemical Property of (1S,4R,5R)-6-(2,4-Dimethoxy-benzyl)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R,5R)-6-(2,4-Dimethoxy-benzyl)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

There total 1 articles about (1S,4R,5R)-6-(2,4-Dimethoxy-benzyl)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 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: 61.0%

phthalimide (136918-14-4,85-41-6) + (1S,4S,5S)-6-(2,4-Dimethoxy-benzyl)-4-hydroxy-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester → (1S,4R,5R)-6-(2,4-Dimethoxy-benzyl)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (269730-12-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1039/a804412k

Reference yield:

(1S,4R,5R)-6-(2,4-Dimethoxy-benzyl)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (269730-12-3) → (1S,4R,5R)-4-Amino-6-(2,4-dimethoxy-benzyl)-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Guidance literature:

With methylhydrazine; In N,N-dimethyl-formamide; at 80 ℃;

DOI:10.1039/a804412k

Reference yield:

(1S,4R,5R)-6-(2,4-Dimethoxy-benzyl)-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (269730-12-3) → (3S,7R,8R,8aS)-7-(benzoylamino)-8-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}octahydro-1,4-dioxopyrrolo[1,2-a]pyrazine-3-acetic acid

Guidance literature:

Multi-step reaction with 11 steps

1: MeNHNH₂ / dimethylformamide / 80 °C

2: Et₃N / CH₂Cl₂

3: 77 percent / K₂S₂O₈, NaH₂PO₄, H₂O / acetonitrile / 78 °C

4: 60 percent / Et₃N, DMAP / CH₂Cl₂

5: Na₂CO₃, H₂O / tetrahydrofuran

6: diethyl ether

7: 96 percent / H₂ / Pd/C / dimethylformamide

8: 80 percent / O-(7-azobenzotriazol-1-yl-)-N,N,N',N'-tetramethyluronium hexafluorophosphate, 1-hydroxy-7-azobenzotriazole, (i-Pr₂)NEt / CH₂Cl₂

9: 100 percent / H₂ / Pd/C / dimethylformamide

10: 89 percent / TFA / CH₂Cl₂

11: 60 percent / (i-Pr)2NEt / CH₂Cl₂

With dmap; sodium dihydrogenphosphate; dipotassium peroxodisulfate; 1-hydroxy-7-aza-benzotriazole; water; hydrogen; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; methylhydrazine; HATU; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/a804412k

upstream raw materials:

phthalimide

Downstream raw materials:

methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate

((3S,7R,8R,8aS)-8-Amino-7-benzoylamino-1,4-dioxo-octahydro-pyrrolo[1,2-a]pyrazin-3-yl)-acetic acid

(1S,4R,5R)-4-Benzoylamino-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

(1S,4R,5R)-4-Benzoylamino-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester