bis[(2-fluorophenyl)methyl] (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate

Base Information

• Chemical Name: bis[(2-fluorophenyl)methyl] (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate
• CAS No.: 1311385-12-2
• Molecular Formula: C₂₇H₂₇F₂NO₇
• Molecular Weight: 515.511
• Mol file: 1311385-12-2.mol

Synonyms:bis[(2-fluorophenyl)methyl] (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate

Chemical Property of bis[(2-fluorophenyl)methyl] (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of bis[(2-fluorophenyl)methyl] (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate

There total 2 articles about bis[(2-fluorophenyl)methyl] (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate 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: 79.0%

o-fluorobenzyl bromide (446-48-0) + (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (1311385-14-4) → bis[(2-fluorophenyl)methyl] (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate (1311385-12-2)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

Reference yield:

(1S,2S,5R,6R)-di-tert-butyl 2-[(tert-butoxycarbonyl)amino]-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate (635318-04-6) → bis[(2-fluorophenyl)methyl] (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate (1311385-12-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 60 °C

1.2: pH 2 - 3 / Cooling with ice

2.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

With water; caesium carbonate; sodium hydroxide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

Reference yield:

bis[(2-fluorophenyl)methyl] (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate (1311385-12-2) → bis[(2-fluorophenyl)methyl] (1S,2S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate (1311385-15-5) + bis[(2-fluorophenyl)methyl] (1S,2S,4R,5R,6R)-2-(tert-butoxycarbonylamino)-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate (1311385-16-6)

Guidance literature:

bis[(2-fluorophenyl)methyl] (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate; With L-Selectride; In tetrahydrofuran; at -78 ℃; for 1.75h; Inert atmosphere;

With water; sodium hydrogencarbonate; In tetrahydrofuran; at -78 ℃;

upstream raw materials:

o-fluorobenzyl bromide

(1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid

(1S,2S,5R,6R)-di-tert-butyl 2-[(tert-butoxycarbonyl)amino]-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate

Downstream raw materials:

Bis[(2-fluorophenyl)methyl] (1S,2S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-4-(p-tolylsulfonyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylate

bis[(2-fluorophenyl)methyl] (1R,2S,4R,5R,6R)-2-(tert-butoxycarbonylamino)-4-(4H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]hexane-2,6-dicarboxylate

bis[(2-fluorophenyl)methyl] (1S,2S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate

bis[(2-fluorophenyl)methyl] (1S,2S,4R,5R,6R)-2-(tert-butoxycarbonylamino)-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate