(-)-(1S,5R)-benzyl-6-(4-methoxyquinolin-8-yl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate

Base Information

Chemical Name:(-)-(1S,5R)-benzyl-6-(4-methoxyquinolin-8-yl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate
CAS No.:1514927-37-7
Molecular Formula:C₂₃H₂₁N₃O₄
Molecular Weight:403.437
Hs Code.:

Synonyms:(-)-(1S,5R)-benzyl-6-(4-methoxyquinolin-8-yl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate

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Chemical Property of (-)-(1S,5R)-benzyl-6-(4-methoxyquinolin-8-yl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate

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Technology Process of (-)-(1S,5R)-benzyl-6-(4-methoxyquinolin-8-yl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate

There total 5 articles about (-)-(1S,5R)-benzyl-6-(4-methoxyquinolin-8-yl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate 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: 86.0%

: 1514927-36-6
(-)-(S)-benzyl 2-((4-methoxyquinolin-8-yl)carbamoyl)pyrrolidine-1-carboxylate

: 1514927-37-7
(-)-(1S,5R)-benzyl-6-(4-methoxyquinolin-8-yl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate

Guidance literature:: With 1,2,3,4,5-pentafluoro-6-iodobenzene; silver(I) acetate; palladium diacetate; at 20 - 160 ℃; Sealed tube; Microwave irradiation;
DOI:10.1021/ol403364k

Reference yield:

: 30465-68-0
5-methoxy-8-aminoquinoline

: 1148-11-4
N-Benzyloxycarbonyl-L-proline

: 1514927-37-7
(-)-(1S,5R)-benzyl-6-(4-methoxyquinolin-8-yl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C

2: palladium diacetate; silver(I) acetate; 1,2,3,4,5-pentafluoro-6-iodobenzene / 20 - 160 °C / Sealed tube; Microwave irradiation

With dmap; 1,2,3,4,5-pentafluoro-6-iodobenzene; silver(I) acetate; palladium diacetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;
DOI:10.1021/ol403364k

Reference yield:

: 147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7
L-proline

: 1514927-37-7
(-)-(1S,5R)-benzyl-6-(4-methoxyquinolin-8-yl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: sodium hydroxide / water / 4 h / 20 °C

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 12 h / 20 °C

3: palladium diacetate; silver(I) acetate; 1,2,3,4,5-pentafluoro-6-iodobenzene / neat (no solvent) / 1.5 h / 160 °C / Microwave irradiation

With dmap; 1,2,3,4,5-pentafluoro-6-iodobenzene; silver(I) acetate; palladium diacetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In dichloromethane; water;
DOI:10.1021/acs.joc.5b02532