N-Isoamyl-N-(6-hydroxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester → N-Isoamyl-N-(6-hydroxy naphthalene-2-sulfonyl)-D-valine

HRID 77319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 77319
C([O:5][C:6](=[O:31])[C@@H:7]([CH:28]([CH3:30])[CH3:29])[N:8]([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:22])[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])(C)(C)C>Cl.C(OCC)(=O)C>[CH2:23]([N:8]([S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:22])[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])[C@@H:7]([C:6]([OH:31])=[O:5])[CH:28]([CH3:30])[CH3:29])[CH2:24][CH:25]([CH3:27])[CH3:26]

Komponenten

4

Edukt 1

HCID 67155390N-Isoamyl-N-(6-hydroxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester

Produkt 1

HCID 67155085N-Isoamyl-N-(6-hydroxy naphthalene-2-sulfonyl)-D-valineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-Isoamyl-N-(6-hydroxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester (0.33 g, 0.74 mmol) is dissolved in 4 N hydrochloric acid in ethyl acetate (50 mL), and the reaction is allowed to stir at ambient temperature for 16 h. The solvent is removed in vacuo, and the residue is purified by column chromatography (15% hexanes-ethyl acetate) to afford the title compound as a colorless oil (0.26 g, 90% yield). LCMS (m/z): (394.24, M+1; 392.27, M−1).

Aufarbeitung

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by column chromatography (15% hexanes-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a3b6b420b2a94a34aed015fcc350f7fa
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841291B2

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