Water → (S)-Ethyl 2-((tert-butoxycarbonyl)amino)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoate

HRID 1454107Notizen

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N1C=CC=CC=1.[F:7][C:8]([F:21])([F:20])[S:9]([O:12]S(C(F)(F)F)(=O)=O)(=[O:11])=[O:10].[CH3:22][C:23]([CH3:43])([O:25][C:26]([NH:28][C@@H:29]([CH2:35][C:36]1[CH:41]=[CH:40][C:39](O)=[CH:38][CH:37]=1)[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:27])[CH3:24].O>ClCCl>[CH3:43][C:23]([CH3:22])([O:25][C:26]([NH:28][C@@H:29]([CH2:35][C:36]1[CH:37]=[CH:38][C:39]([O:12][S:9]([C:8]([F:21])([F:20])[F:7])(=[O:11])=[O:10])=[CH:40][CH:41]=1)[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:27])[CH3:24]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 11077750Ethyl N-(tert-butoxycarbonyl)-L-tyrosinate

Produkt 1

HCID 10789275(S)-Ethyl 2-((tert-butoxycarbonyl)amino)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under nitrogen atmosphere, pyridine(130.3 g) and trifluoromethanesulfonic anhydride (170.4 g) were added dropwise to a solution of ethyl (αS)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxybenzenepropionate (170.0 g) in dichloromethane (1.7 L) at 10° C. or below. After stirring for 1 hour at the same temperature, water (850 ml) was added dropwise to the mixture and the mixture was stirred for 2 hours at the same temperature. The organic layer was washed with 10% aqueous citric acid solution and aqueous saturated sodium hydrogen carbonate solution, and dried over magnesium sulfate. The solvent was removed in vacuo to yield ethyl (αS)-α-[[(1,1-dimethylethoxy)carbonyl]amino]-4-(trifluoromethanesulfonyloxy)benzenepropionate (242.5 g) as oil.

Aufarbeitung

  1. additionwas added dropwise to the mixture
  2. washThe organic layer was washed with 10% aqueous citric acid solution and aqueous saturated sodium hydrogen carbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3e850b3097f0464d998f31c34c3981e3
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07476758B2

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