Potassium Iodide → Methyl 2-(3-tert-Butoxycarbonylaminopropoxy)-4-tert-butylbenzoate

HRID 644289Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 644289
[C:1]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([OH:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:16]([NH:23][CH2:24][CH2:25][CH2:26]Br)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[I-].[K+]>CN(C=O)C>[C:19]([O:18][C:16]([NH:23][CH2:24][CH2:25][CH2:26][O:15][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Komponenten

5

Edukt 3

HCID 4875Potassium IodideHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 20777194Methyl 4-tert-butyl-2-hydroxybenzoate

Produkt 1

HCID 68530190Methyl 2-(3-tert-Butoxycarbonylaminopropoxy)-4-tert-butylbenzoateAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Methyl 4-tert-butyl-2-hydroxybenzoate (2.41 g, 11.6 mmol) was dissolved in DMF (15 mL) and K2 CO3 (2.39 g, 17.4 mmol) and N-Boc-3-bromopropylamine (4.14 g, 17.4 mmol) was added using DMF (10 mL) to aid the transfer. Potassium iodide (0.30 g) was added, and the reaction stirred at room temperature under nitrogen for 18 hr. The DMF was removed in vacuo and the residue taken up in ethyl acetate and washed with water and brine, dried, and the solvent removed in vacuo to give a viscous brown oil. Purification by chromaotgraphy over silica on a preparative scale apparatus, eluting with a gradient of hexane to hexane:ethyl acetate (70:30) gave 1.91 g (45.2%) of a viscous yellow oil.

Aufarbeitung

  1. customThe DMF was removed in vacuo
  2. washwashed with water and brine
  3. customdried
  4. customthe solvent removed in vacuo
  5. customto give a viscous brown oil
  6. customPurification by chromaotgraphy over silica on a preparative scale apparatus
  7. washeluting with a gradient of hexane to hexane:ethyl acetate (70:30)

Quellen und Nachweise

ORD-Eintrag
ord-77670657196546109d8e761506ef5c33
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700628B2

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