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Hydrochloric Acid → [2-fluoro-4-(2-{(1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl}ethoxy)phenyl]acetic acid

HRID 1474697
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1474697
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][C@@H:14]2[CH2:16][C@@H:15]2[CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[N:28]=[CH:27][C:26]([CH2:29][O:30][CH3:31])=[CH:25][N:24]=3)[CH2:19][CH2:18]2)=[CH:7][C:6]=1[F:32].CO.[OH-].[Li+].Cl>O1CCCC1.O>[F:32][C:6]1[CH:7]=[C:8]([O:11][CH2:12][CH2:13][C@@H:14]2[CH2:16][C@@H:15]2[CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[N:24]=[CH:25][C:26]([CH2:29][O:30][CH3:31])=[CH:27][N:28]=3)[CH2:19][CH2:18]2)[CH:9]=[CH:10][C:5]=1[CH2:4][C:3]([OH:33])=[O:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 89583790Methyl{2-fluoro-4-[2-((1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl)ethoxy]phenyl}acetate

Produkt 1

HCID 117678258[2-fluoro-4-(2-{(1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl}ethoxy)phenyl]acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl{2-fluoro-4-[2-((1S,2R)-2-{1-[5-(methoxymethyl)pyrimidin-2-yl]piperidin-4-yl}cyclopropyl)ethoxy]phenyl}acetate (1.50 g, 3.28 mmol) in 21 ml of tetrahydrofuran was added 14 ml of methanol and 14 ml of water. Lithium hydroxide (0.393 g, 16.4 mmol) was added to the mixture, and stirred at RT overnight. 1 M hydrochloric acid was added to adjust the pH to 4. The volatiles were removed in vacuo, and the remaining aqueous layer extracted with dichloromethane (3×30 ml). The organic fractions were combined, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (50 g silica gel) using a gradient eluent of 0-70% ethyl acetate in hexanes (1000 ml) to afford the title compound. LC/MS (m/z) 444.4 (M+H)+.

Aufarbeitung

  1. customThe volatiles were removed in vacuo
  2. extractionthe remaining aqueous layer extracted with dichloromethane (3×30 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (50 g silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-96edfffa047c4de38f87f02601228922
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09018224B2

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