methyl 5-oxo-4-(methyloxycarbonyl)-2-[N-(9-phenylfluoren-9-yl)amino]hexanoate

Base Information

• Chemical Name: methyl 5-oxo-4-(methyloxycarbonyl)-2-[N-(9-phenylfluoren-9-yl)amino]hexanoate
• CAS No.: 296774-83-9
• Molecular Formula: C₂₈H₂₇NO₅
• Molecular Weight: 457.526
• Mol file: 296774-83-9.mol

Synonyms:methyl 5-oxo-4-(methyloxycarbonyl)-2-[N-(9-phenylfluoren-9-yl)amino]hexanoate

Chemical Property of methyl 5-oxo-4-(methyloxycarbonyl)-2-[N-(9-phenylfluoren-9-yl)amino]hexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-oxo-4-(methyloxycarbonyl)-2-[N-(9-phenylfluoren-9-yl)amino]hexanoate

There total 2 articles about methyl 5-oxo-4-(methyloxycarbonyl)-2-[N-(9-phenylfluoren-9-yl)amino]hexanoate 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%

acetoacetic acid methyl ester (105-45-3) + (4S)-methyl 2,2-dioxo-3-(9-(9-phenylfluorenyl))-1,2,3-oxathiazolidine-4-carboxylate (296774-94-2) → methyl 5-oxo-4-(methyloxycarbonyl)-2-[N-(9-phenylfluoren-9-yl)amino]hexanoate (296774-83-9)

Guidance literature:

acetoacetic acid methyl ester; With sodium hydride; In 1,2-dimethoxyethane; for 0.166667h;

(4S)-methyl 2,2-dioxo-3-(9-(9-phenylfluorenyl))-1,2,3-oxathiazolidine-4-carboxylate; In 1,2-dimethoxyethane; at 60 ℃; for 18h;

DOI:10.1139/v00-176

Reference yield:

(2RS,4S)-methyl 2-oxo-3-(9-phenylfluoren-9-yl)-1,2,3-oxathiazolidine-4-carboxylate → methyl 5-oxo-4-(methyloxycarbonyl)-2-[N-(9-phenylfluoren-9-yl)amino]hexanoate (296774-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 87 percent / RuCl₃*H₂O; NaIO₄ / acetonitrile; H₂O / 4 h / 0 °C

2.1: NaH / 1,2-dimethoxy-ethane / 0.17 h

2.2: 86 percent / 1,2-dimethoxy-ethane / 18 h / 60 °C

With ruthenium trichloride; sodium periodate; sodium hydride; In 1,2-dimethoxyethane; water; acetonitrile;

DOI:10.1139/v00-176

Reference yield:

methyl 5-oxo-4-(methyloxycarbonyl)-2-[N-(9-phenylfluoren-9-yl)amino]hexanoate (296774-83-9) → (2R,5R)-2-Methyl-5-(1-phenyl-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 5 steps

1: NaOH / ethanol / 5 h / Heating

2: 259 mg / K₂CO₃ / acetonitrile / 18 h / 20 °C

3: 92 percent / H₂ / Pd/C / methanol / 48 h / 3040.2 Torr

4: 96 percent / KOSiMe₃ / diethyl ether / 18 h / 20 °C

5: TBTU / acetonitrile / 2 h

With sodium hydroxide; potassium trimethylsilonate; hydrogen; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; palladium on activated charcoal; In methanol; diethyl ether; ethanol; acetonitrile; 1: Decarboxylation / 2: Esterification / 3: Hydrogenolysis / 4: ester cleavage / 5: Acylation;

DOI:10.1021/ol006102b

upstream raw materials:

acetoacetic acid methyl ester

(4S)-methyl 2,2-dioxo-3-(9-(9-phenylfluorenyl))-1,2,3-oxathiazolidine-4-carboxylate

Downstream raw materials:

cis-5-methylproline

cis-N-(Boc)-5-methylproline

methyl 5-oxo-2-[N-(9-(9-phenylfluorenyl))amino]hexanoate