tert-Butanol → Ethyl 3-[2-(t-butoxycarbonylamino)ethyl]-5-[(4-fluorophenyl)methyl]benzenepropanoate

HRID 53330Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 53330
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11](CCC([O-])=O)[CH:12]=[C:13]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:14]=2)=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.C([N:46]([CH2:49]C)[CH2:47][CH3:48])C.[C:51]([OH:55])([CH3:54])([CH3:53])[CH3:52]>>[C:51]([O:55][C:49]([NH:46][CH2:47][CH2:48][C:11]1[CH:12]=[C:13]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:14]=[C:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:10]=1)=[O:34])([CH3:54])([CH3:53])[CH3:52]

Komponenten

5

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 86750692Monoethyl 5-[(4-fluorophenyl)-methyl]-1,3-benzenedipropanoate

Produkt 1

HCID 19962360Ethyl 3-[2-(t-butoxycarbonylamino)ethyl]-5-[(4-fluorophenyl)methyl]benzenepropanoate

Versuchsvorschrift

A solution of monoethyl 5-[(4-fluorophenyl)-methyl]-1,3-benzenedipropanoate (3.0 g), diphenyl-phosphoryl azide (2.51 g) and triethylamine (1.3 ml) in dry t-butanol (25 ml) was stirred at room temperature for 15 minutes and then heated under reflux for 20 hours. The solution was evaporated and the residue was partitioned between ether and wateT. The ether layer was separated, dried (MgSO4) and evaporated to give an oil which was chromatographed on silica gel. Elution with dichloromethane gave the title compound as a gum (2.41 g), Rf 0.2(SS 3). N.M.R. δ(CDCl3): 1.23(3H,t), 1.44(9H,s), 2.58(2H,t), 2.72(2H,t), 2.88(2H,t), 3.32(2H,m), 3.89(2H,s), 4.10(2H,q), 4.50(1H,br), 6.82-6.90(3H), 6.94-7.0(2H,m), 7.09-7.15(2H,m).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 20 hours
  3. customThe solution was evaporated
  4. customthe residue was partitioned between ether and wateT
  5. customThe ether layer was separated
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give an oil which
  9. customwas chromatographed on silica gel
  10. washElution with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-b047db079ee84a9d98cbc5b907eb38f1
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618941

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