Methanesulfonic Acid → (2R)-2-phenylcarbonyloxypropyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate mesylate

HRID 229498

Reaktionsgleichung

Reaktionsgleichung von HRID 229498
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].C(OC([NH:13][C@@H:14]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([OH:38])[CH:32]=1)[C:15]([O:17][CH2:18][C@H:19]([O:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23])[CH3:20])=[O:16])=O)(C)(C)C.C(OC)(C)(C)C>O1CCOCC1>[S:2]([OH:5])(=[O:4])(=[O:3])[CH3:1].[NH2:13][C@@H:14]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([OH:38])[CH:32]=1)[C:15]([O:17][CH2:18][C@H:19]([O:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23])[CH3:20])=[O:16]

Komponenten

5

Edukt 3

HCID 6395Methanesulfonic AcidHCID 15413tert-Butyl methyl etherHCID 46899463(2R)-2-Phenylcarbonyloxypropyl(2S)-2-(tert-Butoxycarbonyl)amino-3-(3,4-dihydroxyphenyl)propanoate

Produkt 1

HCID 16125134(2R)-2-phenylcarbonyloxypropyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate mesylateAusbeute 54,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Methanesulfonic acid (3.9 mL, 60.1 mmol) was slowly added to a solution of (2R)-2-phenylcarbonyloxypropyl (2S)-2-(tert-butoxycarbonyl)amino-3-(3,4-dihydroxyphenyl)propanoate 2 (11.0 g, 22.1 mmol) in 1,4-dioxane (30 mL) while stirred at room temperature. The reaction mixture was stirred for 2 h. The solution was slowly added to methyl tert-butyl ether (MTBE) (600 mL) with vigorous stirring. The resulting suspension was filtered. The filter cake washed three times with methyl tert-butyl ether and air dried to afford 5.48 g (54% yield) of the mesylate salt 1 as an off-white solid.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 2 h
  2. filtrationThe resulting suspension was filtered
  3. washThe filter cake washed three times with methyl tert-butyl ether and air
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-38df535ce57b4382946827761e42178a
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563821B2

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