methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(2,4-difluorophenyl)-5-oxazolidinecarboxylate

Base Information

Chemical Name:methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(2,4-difluorophenyl)-5-oxazolidinecarboxylate
CAS No.:174729-95-4
Molecular Formula:C₁₈H₂₃F₂NO₅
Molecular Weight:371.381
Hs Code.:

Synonyms:methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(2,4-difluorophenyl)-5-oxazolidinecarboxylate

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Chemical Property of methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(2,4-difluorophenyl)-5-oxazolidinecarboxylate

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Technology Process of methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(2,4-difluorophenyl)-5-oxazolidinecarboxylate

There total 7 articles about methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(2,4-difluorophenyl)-5-oxazolidinecarboxylate 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: 74.0%

: 116-11-0
2-Methoxypropene

: 174729-94-3
methyl (2R,3S)-3-(2,4-difluorophenyl)-3-tert-butoxycarbonylamino-2-hydroxypropionate

: 174729-95-4
methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(2,4-difluorophenyl)-5-oxazolidinecarboxylate

Guidance literature:: With pyridinium p-toluenesulfonate; In benzene; at 90 ℃;
DOI:10.3987/com-96-s20

Reference yield:

: 186758-21-4,166883-00-7
methyl (2E)-3-(2,4-difluorophenyl)prop-2-enoate

: 174729-95-4
methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(2,4-difluorophenyl)-5-oxazolidinecarboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 71 percent / K₃Fe(CN)6, K₂CO₃, (DHQ)2PHAL, osmium tetroxide / 2-methyl-propan-2-ol; H₂O / 18 h / Ambient temperature

2: p-TsOH*H₂O / CH₂Cl₂ / 2.5 h / Ambient temperature

3: SnBr₂ / CH₂Cl₂ / -15 deg C, 1 h then 0 deg C, 2 h

4: 75 percent / sodium azide / dimethylformamide / 2.5 h / 40 °C

5: 73 percent / K₂CO₃ / methanol / 0.33 h / 0 °C

6: 91 percent / H₂ / Pd/C / ethyl acetate / 3.5 h / 760 Torr / Ambient temperature

7: 74 percent / pyridinium p-toluenesulfonate / benzene / 90 °C

With osmium(VIII) oxide; sodium azide; Hydroquinone 1,4-phthalazinediyl diether; hydrogen; pyridinium p-toluenesulfonate; tin(II) bromide; potassium carbonate; toluene-4-sulfonic acid; potassium hexacyanoferrate(III); palladium on activated charcoal; In methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.3987/com-96-s20

Reference yield:

: 186758-22-5
(2R,3S)-3-(2,4-Difluoro-phenyl)-2,3-dihydroxy-propionic acid methyl ester

: 174729-95-4
methyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-(2,4-difluorophenyl)-5-oxazolidinecarboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: p-TsOH*H₂O / CH₂Cl₂ / 2.5 h / Ambient temperature

2: SnBr₂ / CH₂Cl₂ / -15 deg C, 1 h then 0 deg C, 2 h

3: 75 percent / sodium azide / dimethylformamide / 2.5 h / 40 °C

4: 73 percent / K₂CO₃ / methanol / 0.33 h / 0 °C

5: 91 percent / H₂ / Pd/C / ethyl acetate / 3.5 h / 760 Torr / Ambient temperature

6: 74 percent / pyridinium p-toluenesulfonate / benzene / 90 °C

With sodium azide; hydrogen; pyridinium p-toluenesulfonate; tin(II) bromide; potassium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.3987/com-96-s20