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

HRID 1869847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869847
C[O:2][C:3](=[O:34])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:15]=[C:16]3[C:21](=[C:22]([CH2:24][N:25]([CH:27]4[CH2:29][CH2:28]4)[CH3:26])[CH:23]=2)[O:20][C:19]([CH3:31])([CH3:30])[CH2:18][C:17]3([CH3:33])[CH3:32])=[CH:8][CH:7]=1)[CH3:5].[OH-].[Na+]>CO.O1CCCC1>[CH:27]1([N:25]([CH2:24][C:22]2[CH:23]=[C:14]([C:13]#[C:12][C:9]3[CH:10]=[CH:11][C:6]([CH:4]([CH3:5])[C:3]([OH:34])=[O:2])=[CH:7][CH:8]=3)[CH:15]=[C:16]3[C:21]=2[O:20][C:19]([CH3:30])([CH3:31])[CH2:18][C:17]3([CH3:33])[CH3:32])[CH3:26])[CH2:29][CH2:28]1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 690760872-(4-{8-[(Cyclopropyl-methyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman-6-ylethynyl}-phenyl)-propionic acid methyl ester2×

Produkt 1

HCID 112361692-(4-{8-[(Cyclopropyl-methyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman-6-ylethynyl}-phenyl)-propionic acidAusbeute 45 %

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)-propionic acid methyl ester (Intermediate 14, 0.057 g, 0.12 mmol) in methanol (1 mL) and tetrahydrofuran (3 mL) was treated with a 1M solution of sodium hydroxide (0.3 mL, 0.3 mmol) and the resulting reaction mixture was stirred at ambient temperature overnight. The volatiles were evaporated in vacuo to a residue that was washed with hexane, 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 afford the title product as a yellow solid (0.024 g, 45%).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo to a residue that
  3. washwas washed with hexane
  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

Quellen und Nachweise

ORD-Eintrag
ord-60028fea116140ffa1eca997f0439062
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638648B2

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