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

HRID 1683354

반응식

HRID 1683354 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
20 °C

실험 절차

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:

후처리

  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

출처 및 근거

ORD 기록
ord-c7eed6b15d1a427aa270f3bb9bc5b152
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05637723

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