Sodium Hydroxide → 2-(4-{8-[(Cyclopropyl-methyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman-6-ylethynyl}-phenyl)-2-methyl-propionic acid

HRID 1869849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869849
C[O:2][C:3](=[O:35])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:16]=[C:17]3[C:22](=[C:23]([CH2:25][N:26]([CH:28]4[CH2:30][CH2:29]4)[CH3:27])[CH:24]=2)[O:21][C:20]([CH3:32])([CH3:31])[CH2:19][C:18]3([CH3:34])[CH3:33])=[CH:9][CH:8]=1)([CH3:6])[CH3:5].[OH-].[Na+]>CO.O1CCCC1>[CH:28]1([N:26]([CH2:25][C:23]2[CH:24]=[C:15]([C:14]#[C:13][C:10]3[CH:11]=[CH:12][C:7]([C:4]([CH3:6])([CH3:5])[C:3]([OH:35])=[O:2])=[CH:8][CH:9]=3)[CH:16]=[C:17]3[C:22]=2[O:21][C:20]([CH3:32])([CH3:31])[CH2:19][C:18]3([CH3:33])[CH3:34])[CH3:27])[CH2:30][CH2:29]1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 690741872-(4-{8-[(Cyclopropyl-methyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman-6-ylethynyl}-phenyl)-2-methyl-propionic acid methyl ester2×

Produkt 1

HCID 112133162-(4-{8-[(Cyclopropyl-methyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman-6-ylethynyl}-phenyl)-2-methyl-propionic acidAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-(4-{8-[(cyclopropyl-methyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman-6-ylethynyl}-phenyl)-2-methyl-propionic acid methyl ester (Intermediate 15, 0.040 g, 0.084 mmol) in methanol (2.5 mL) and tetrahydrofuran (2.5 mL) was treated with a 2M solution of sodium hydroxide (1 mL, 2 mmol) and the resulting reaction mixture was refluxed overnight. The volatiles were evaporated in vacuo to a residue that was neutralized with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was washed with water and brine, and dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to an oil. Preparative reverse phase HPLC on a partisil 10 ODS-3 column using 10% water in acetonitrile as the mobile phase afforded the title compound (0.008 g, 27%).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed overnight
  3. customThe volatiles were evaporated in vacuo to a residue that
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo to an oil

Quellen und Nachweise

ORD-Eintrag
ord-1b5c380048ca44beba5fcf7a3152f3f2
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638648B2

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