Sodium hydride → ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenoxy]hexanoate

HRID 1290533

Reaktionsgleichung

Reaktionsgleichung von HRID 1290533
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([N:9]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:5][CH:4]=1.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CN(C=O)C>[N:3]1[CH:8]=[CH:7][C:6]([N:9]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:21][CH:22]=2)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 117544Ethyl 6-bromohexanoateHCID 18918286tert-butyl N-(4-hydroxyphenyl)-N-(pyridin-4-yl)carbamate

Produkt 1

HCID 18918347ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenoxy]hexanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (50% w/w dispersion in mineral oil, 55 mg) was added under argon to a stirred solution of the product from step iii) above (300 mg)in dry DMF (5 ml). After five minutes, ethyl 6-bromohexanoate (0.20 ml) was added and the mixture stirred for 16 hours. The DMF was evaporated in vacuo and the residue partitioned between dichloromethane and water. The aqueous phase was extracted with further dichloromethane. The combined organic extracts were washed with water then dried, and evaporated. The residue was purified by chromatography on alumina, eluting with dichloromethane and the 1% v/v methanol/dichloromethane. Evaporation of the appropriate fractions gave ethyl 6-[4-[N-(4-pyridyl)-N-tertiary-butyloxycarbonylamino]phenoxy]hexanoate, 260 mg, as a yellow gum: NMR (CDCl3) δ8.40(2H,dd), 7.16(2H,dd), 7.07(2H,m), 6.90(2H,m), 4.13(2H,q), 3.98(2H,t), 2.34(2H,t), 1.78(4H,m), 1.57(2H,m), 1.44(9H,s), 1.26(3H;t); m/e 429 (M+H)+.

Aufarbeitung

  1. customThe DMF was evaporated in vacuo
  2. customthe residue partitioned between dichloromethane and water
  3. extractionThe aqueous phase was extracted with further dichloromethane
  4. washThe combined organic extracts were washed with water
  5. customthen dried
  6. customevaporated
  7. customThe residue was purified by chromatography on alumina
  8. washeluting with dichloromethane
  9. customEvaporation of the appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-e8e95f30566c4cfdae72332afec0f2ef
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750754

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