Ethyl Acetate → ethyl (4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-cyclopropyl-5-oxazolidinecarboxylate

HRID 1082191ノート

反応式

HRID 1082191 の反応式
[CH:1]1([C@H:4]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:5]([OH:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH3:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([CH:45](OC)OC)=[CH:41][CH:40]=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[C:16]([O:15][C:13]([N:12]1[C@@H:4]([CH:1]2[CH2:3][CH2:2]2)[C@H:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[O:11][CH:45]1[C:42]1[CH:43]=[CH:44][C:39]([O:38][CH3:37])=[CH:40][CH:41]=1)=[O:14])([CH3:18])([CH3:17])[CH3:19]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 75140p-(Dimethoxymethyl)anisoleHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 53968179HCID 53968179、化合物

生成物 1

HCID 53715740ethyl (4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-cyclopropyl-5-oxazolidinecarboxylate収率 53%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

A solution of 2.07 g of ethyl (2R,3S)-3-cyclopropyl-3-tert -butoxycarbonylamino-2-hydroxypropionate and 213 mg of pyridinium p-toluenesulfonate in 125 ml of toluene is refluxed under heating. To the mixture is added dropwise a solution of 2.76 g of p-anisaldehydedimethylacetal in 25 ml of toluene for 20 minutes. The reaction mixture is evaporated to remove the generated methanol. The mixture is stirred under heating for 1.5 hours and cooled. After the reaction mixture is condensed under reduced pressure, ethyl acetate and water are added to the residue. The ethyl acetate layer is obtained by separation. The aqueous layer is extracted with ethyl acetate. The extract is washed with water and brine, dried and condensed under reduced pressure. The residue is purified by silica gel column chromatography (solvent; toluene:ethyl acetate=40:1) to give 1.572 g of ethyl (4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-cyclopropyl-5-oxazolidinecarboxylate (diastereomeric mixture).

後処理

  1. temperatureunder heating
  2. customThe reaction mixture is evaporated
  3. customto remove the generated methanol
  4. temperatureunder heating for 1.5 hours
  5. temperaturecooled
  6. customcondensed under reduced pressure, ethyl acetate and water
  7. additionare added to the residue
  8. extractionThe aqueous layer is extracted with ethyl acetate
  9. washThe extract is washed with water and brine
  10. customdried
  11. customcondensed under reduced pressure
  12. customThe residue is purified by silica gel column chromatography (solvent; toluene:ethyl acetate=40:1)

出典と根拠

ORDレコード
ord-56076321642345e0acb1a5510adf42eb
出典データセット
uspto-grants-1996_12
特許番号
US05589502

反応ノート

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