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Hydrochloric Acid → (2S)-3-[tert-butoxycarbonyl(methyl)amino]-2-(5-chloro-2-methoxybenzyl)propanoic acid

HRID 80575
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 80575
[H-].[Na+].[CH3:3]I.[C:5]([O:9][C:10]([NH:12][CH2:13][C@H:14]([CH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[O:26][CH3:27])[C:15]([OH:17])=[O:16])=[O:11])([CH3:8])([CH3:7])[CH3:6].Cl>C(OCC)(=O)C.O.O1CCCC1>[C:5]([O:9][C:10]([N:12]([CH3:3])[CH2:13][C@H:14]([CH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[O:26][CH3:27])[C:15]([OH:17])=[O:16])=[O:11])([CH3:8])([CH3:7])[CH3:6]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66935162(2S)-3-[(tert-butoxycarbonyl)amino]-2-(5-chloro-2-methoxybenzyl)propanoic acid

Produkt 1

HCID 70815183(2S)-3-[tert-butoxycarbonyl(methyl)amino]-2-(5-chloro-2-methoxybenzyl)propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a 60% mineral oil dispersion of sodium hydride (1.9 g) in a tetrahydrofuran (50 ml) solution, methyl iodide (2.7 ml) was added under ice cooling, then the (2S)-3-[(tert-butoxycarbonyl)amino]-2-(5-chloro-2-methoxybenzyl)propanoic acid (5 g), described in WO 06-059801A, in a tetrahydrofuran (20 ml) solution was slowly added, then the mixture was stirred at room temperature for 72 hours. To the reaction solution, water (50 ml) and ethyl acetate (20 ml) were added and the layers were separated. The organic layer was extracted with water (20 ml) and was combined with the aqueous layer previously obtained, and acidified (pH2) with 6M hydrochloric acid. This aqueous mixture was extracted with ethyl acetate, then the combined extract was washed with water, saturated aqueous sodium thiosulfate solution, and brine. The organic layer was dried over sodium sulfate, then concentrated to obtain (2S)-3-[tert-butoxycarbonyl(methyl)amino]-2-(5-chloro-2-methoxybenzyl)propanoic acid (5.28 g) (compound S17a).

Aufarbeitung

  1. additionwas slowly added
  2. customthe layers were separated
  3. extractionThe organic layer was extracted with water (20 ml)
  4. custompreviously obtained
  5. extractionThis aqueous mixture was extracted with ethyl acetate
  6. extractionthe combined extract
  7. washwas washed with water, saturated aqueous sodium thiosulfate solution, and brine
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-892ae960d71a4f4f9320582340aba907
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846660B2

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