Methyl 2-benzylprop-2-enoate → Methyl alpha-[[hydroxy[1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]benzenepropanoate

HRID 1058770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1058770
[PH2:1](=[O:3])[OH:2].[C:4]1([CH2:10][C:11](=[CH2:16])[C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:17]/[C:18](/O[Si](C)(C)C)=[N:19]\[Si](C)(C)C.[C:29]([O:32][CH2:33][CH3:34])(=[O:31])C.O>C(#N)C>[OH:3][P:1]([CH2:16][CH:11]([CH2:10][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:12]([O:14][CH3:15])=[O:13])([CH:18]([NH:19][C:29]([O:32][CH2:33][C:34]1[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=1)=[O:31])[CH3:17])=[O:2]

Komponenten

6

Edukt 4

HCID 575761Methyl 2-benzylprop-2-enoateHCID 4124402Phosphinic AcidHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 22728543Water ethylacetate

Produkt 1

HCID 18668704Methyl alpha-[[hydroxy[1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]benzenepropanoateAusbeute 68,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 0.6 g (2.47 mmol) of 1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid, 2.17 g (12.3 mmol) of methyl 2-(phenylmethyl)propenoate and 0.52 ml of N,O-bis(trimethylsilyl)acetamide in 0.27 ml of acetonitrile is stirred at a temperature in the region of 20° C. for 24 hours. 60 ml of a 1/1 ethyl acetate/water mixture are added. The aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with water, dried over sodium sulphate, filtered and evaporated off under vacuum. The product is purified by recrystallization from a mixture of ethyl acetate and hexane. 0.71 g of product are recovered (yield=68.9%).

Aufarbeitung

  1. extractionThe aqueous phase is extracted with ethyl acetate
  2. washThe combined organic phases are washed with water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated off under vacuum
  6. customThe product is purified by recrystallization from a mixture of ethyl acetate and hexane
  7. custom0.71 g of product are recovered (yield=68.9%)

Quellen und Nachweise

ORD-Eintrag
ord-edf37c17871546aebbe58bab8a274b28
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518260B1

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