Trimethyl orthoformate → (4S,5R)-3-t-butoxycarbonyl-2-methoxy-4-phenyl-5-methoxycarbonyl-1,3-oxazolidine

HRID 1683354

反応式

HRID 1683354 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@@H:10]([OH:15])[C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH:39](OC)(OC)[O:40][CH3:41]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C@@H:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C@H:10]([C:11]([O:13][CH3:14])=[O:12])[O:15][CH:39]1[O:40][CH3:41])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 9005Trimethyl orthoformateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 11140973Methyl (alphaR,betaS)-beta-(((1,1-dimethylethoxy)carbonyl)amino)-alpha-hydroxybenzenepropanoate

生成物 1

HCID 57061955(4S,5R)-3-t-butoxycarbonyl-2-methoxy-4-phenyl-5-methoxycarbonyl-1,3-oxazolidine収率 40%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
20 °C

実験手順

A solution of 10.0 g of methyl (2R,3S)-3-t-butoxycarbonylamino-2-hydroxy-3-phenylpropionate, 0.334 g of pyridinium p-toluenesulphonate and 3.75 cm3 of trimethyl orthoformate in 70 cm3 of toluene is heated to reflux. 4 cm3 of solvent are distilled off. After cooling to a temperature in the region of 20° C. and filtration, the filtrate is concentrated to dryness under reduced pressure. The residue is taken up with 50 cm3 of hexane. The slurry obtained is filtered, rinsed and drained. 4.6 g of (4S,5R)-3-t-butoxycarbonyl-2-methoxy-4-phenyl-5-methoxycarbonyl-1,3-oxazolidine are thereby obtained in a 40% yield in the form of a mixture of diastereoisomers, the characteristics of which are as follows:

後処理

  1. distillation4 cm3 of solvent are distilled off
  2. concentrationthe filtrate is concentrated to dryness under reduced pressure
  3. customThe slurry obtained
  4. filtrationis filtered
  5. washrinsed

出典と根拠

ORDレコード
ord-c7eed6b15d1a427aa270f3bb9bc5b152
出典データセット
uspto-grants-1997_06
特許番号
US05637723

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