tert-butyl (R)-dimethyl-4-[2,6-dichloro-4-(2'-iodo-3',5'-dimethoxybenzoyloxy)-phenyl]-oxazolidine-N-carboxylate

Base Information

Chemical Name:tert-butyl (R)-dimethyl-4-[2,6-dichloro-4-(2'-iodo-3',5'-dimethoxybenzoyloxy)-phenyl]-oxazolidine-N-carboxylate
CAS No.:461031-86-7
Molecular Formula:C₂₅H₂₈Cl₂INO₇
Molecular Weight:652.31
Hs Code.:

Synonyms:tert-butyl (R)-dimethyl-4-[2,6-dichloro-4-(2'-iodo-3',5'-dimethoxybenzoyloxy)-phenyl]-oxazolidine-N-carboxylate

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Chemical Property of tert-butyl (R)-dimethyl-4-[2,6-dichloro-4-(2'-iodo-3',5'-dimethoxybenzoyloxy)-phenyl]-oxazolidine-N-carboxylate

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Technology Process of tert-butyl (R)-dimethyl-4-[2,6-dichloro-4-(2'-iodo-3',5'-dimethoxybenzoyloxy)-phenyl]-oxazolidine-N-carboxylate

There total 2 articles about tert-butyl (R)-dimethyl-4-[2,6-dichloro-4-(2'-iodo-3',5'-dimethoxybenzoyloxy)-phenyl]-oxazolidine-N-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: 85.0%

: (4R/S)-N-(tert-butoxycarbonyl)-2,2'-dimethyl-4-[(4-hydroxy)-2,6-dichlorophenyl]-1,3-oxazoline

: 124481-00-1
2-iodo-3,5-dimethoxybenzoic acid

: 461031-86-7
tert-butyl (R)-dimethyl-4-[2,6-dichloro-4-(2'-iodo-3',5'-dimethoxybenzoyloxy)-phenyl]-oxazolidine-N-carboxylate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 45h;
DOI:10.1021/ol026182e

Reference yield:

: 114605-46-8
methyl 2-iodo-3,5-dimethoxybenzoate

: 461031-86-7
tert-butyl (R)-dimethyl-4-[2,6-dichloro-4-(2'-iodo-3',5'-dimethoxybenzoyloxy)-phenyl]-oxazolidine-N-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / aq. NaOH / methanol; ethanol / 1 h / 70 - 80 °C

2: 85 percent / DCC; DMAP / dimethylformamide / 45 h / 0 - 20 °C

With dmap; sodium hydroxide; dicyclohexyl-carbodiimide; In methanol; ethanol; N,N-dimethyl-formamide;
DOI:10.1021/ol026182e

Reference yield:

: 461031-86-7
tert-butyl (R)-dimethyl-4-[2,6-dichloro-4-(2'-iodo-3',5'-dimethoxybenzoyloxy)-phenyl]-oxazolidine-N-carboxylate

: tert-butyl (P,R)-2,2-dimethyl-4-[(2,6-dichloro-4-hydroxy-3',5'-dimethoxy-1'-hydroxymethyl)-(3,2'-biphenyl)-1-yl]-oxazolidine-N-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: Pd(OAc)2; PPh₃; NaOPiv / 1 h / 20 °C / 0.01 Torr

1.2: 64 percent / DMA / 1 h / 100 °C

2.1: (3aS)-1-Me-3,3-di-Ph-tetraH-pyrrolo[1,2-c][1,2,3]oxazaborole; BH₃*THF / toluene / 1.5 h / -25 °C

With palladium diacetate; borane-THF; sodium pivalate; triphenylphosphine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In toluene;
DOI:10.1021/ol026182e