ethyl (4S,3'S)-2-oxo-3-(9-phenylfluoren-9-yl)oxazolidine-4-(2',2'-difluoro-3'-hydroxy)propanoate

Base Information

• Chemical Name: ethyl (4S,3'S)-2-oxo-3-(9-phenylfluoren-9-yl)oxazolidine-4-(2',2'-difluoro-3'-hydroxy)propanoate
• CAS No.: 371155-39-4
• Molecular Formula: C₂₇H₂₃F₂NO₅
• Molecular Weight: 479.48

Synonyms:ethyl (4S,3'S)-2-oxo-3-(9-phenylfluoren-9-yl)oxazolidine-4-(2',2'-difluoro-3'-hydroxy)propanoate

Chemical Property of ethyl (4S,3'S)-2-oxo-3-(9-phenylfluoren-9-yl)oxazolidine-4-(2',2'-difluoro-3'-hydroxy)propanoate

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Technology Process of ethyl (4S,3'S)-2-oxo-3-(9-phenylfluoren-9-yl)oxazolidine-4-(2',2'-difluoro-3'-hydroxy)propanoate

There total 2 articles about ethyl (4S,3'S)-2-oxo-3-(9-phenylfluoren-9-yl)oxazolidine-4-(2',2'-difluoro-3'-hydroxy)propanoate 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:

Ethyl bromodifluoroacetate (667-27-6) + (4S)-2-oxo-3-(9-phenylfluoren-9-yl)oxazolidine-4-carboxaldehyde (122213-54-1) → ethyl (4S,3'S)-2-oxo-3-(9-phenylfluoren-9-yl)oxazolidine-4-(2',2'-difluoro-3'-hydroxy)propanoate (371155-39-4) + ethyl (4S,3'R)-2-oxo-3-(9-phenylfluoren-9-yl)oxazolidine-4-(2',2'-difluoro-3'-hydroxy)propanoate

Guidance literature:

With zinc; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jo015754q

Reference yield:

2-oxo-3-(9-phenyl-9H-fluoren-9-yl)-oxazolidine-4-carboxylic acid methyl ester → ethyl (4S,3'S)-2-oxo-3-(9-phenylfluoren-9-yl)oxazolidine-4-(2',2'-difluoro-3'-hydroxy)propanoate (371155-39-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / LiAlH₄ / tetrahydrofuran / 2 h / -78 - -75 °C

2: Zn powder / tetrahydrofuran / 2 h / 20 °C

With lithium aluminium tetrahydride; zinc; In tetrahydrofuran;

DOI:10.1021/jo015754q

Reference yield: 98.0%

dimethyl amine (124-40-3) + ethyl (4S,3'S)-2-oxo-3-(9-phenylfluoren-9-yl)oxazolidine-4-(2',2'-difluoro-3'-hydroxy)propanoate (371155-39-4) → N,N-dimethyl (4S,3'S)-2-oxo-3-(9-phenylfluoren-9-yl)oxazolidine-4-(2',2'-difluoro-3'-hydroxy)propionamide (371155-38-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at 20 ℃; for 1.5h;

DOI:10.1021/jo015754q

upstream raw materials:

Ethyl bromodifluoroacetate

(4S)-2-oxo-3-(9-phenylfluoren-9-yl)oxazolidine-4-carboxaldehyde

Downstream raw materials:

N,N-dimethyl (4S,3'S)-2-oxo-3-(9-phenylfluoren-9-yl)oxazolidine-4-(2',2'-difluoro-3'-hydroxy)propionamide

thiocarbonic acid O-{2-dimethylcarbamoyl-2,2-difluoro-1-[2-oxo-3-(9-phenyl-9H-fluoren-9-yl)-oxazolidin-4-yl]-ethyl} ester O-pentafluorophenyl ester

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