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Sodium Iodide → N-[3,5-bis[(1-oxodecyl)amino]phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester

HRID 1110226
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1110226
[NH2:1][C:2]1[CH:3]=[C:4]([NH:20][C:21](=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:5]=[C:6]([NH:8][C:9](=[O:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:7]=1.Br[CH2:33][C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35].CN(C)[C:46]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][C:54]=2N(C)C)C=CC=1.[I-].[Na+]>C(#N)C.CN(C=O)C>[C:38]1([CH2:37][O:36][C:34](=[O:35])[CH2:33][N:1]([C:2]2[CH:3]=[C:4]([NH:20][C:21](=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:5]=[C:6]([NH:8][C:9](=[O:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:7]=2)[CH2:33][C:34](=[O:35])[O:36][CH2:46][C:55]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 62576Benzyl bromoacetateHCID 88675Proton spongeHCID 19389144N,N'-(5-amino-1,3-phenylene)bisdecanamide

Produkt 1

HCID 19389157N-[3,5-bis[(1-oxodecyl)amino]phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl esterAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 1.92 g (4.45 mmol) of N,N'-(5-amino-1,3-phenylene)bisdecanamide, 10.6 ml (0.061 mol) of benzyl bromoacetate, 2.4 g (11.1 mmol) of 1,8-bis(dimethylamino)-naphthalene and 0.19 g (1.25 mmol) of sodium iodide in 50 ml of acetonitrile and 15 ml of DMF was stirred and refluxed under an argon atmosphere for 36 hours. The solvents were removed at reduced pressure and the residue was dissolved in ethyl acetate. The extract was washed with 0.05N HCl, with NaHCO3 solution, dried and concentrated to a brown solid. Purification by HPLC using 25% ethyl acetate-hexane gave 0.9 g which was recrystallized from acetone-hexane to give 0.064 g (20% yield, mp 127°-129°) of N-[3,5-bis[(1-oxodecyl)amino]phenyl]-N-[2-oxo-2-(phenylmethoxy)ethyl]glycine phenylmethyl ester.

Aufarbeitung

  1. temperaturerefluxed under an argon atmosphere for 36 hours
  2. customThe solvents were removed at reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe extract was washed with 0.05N HCl, with NaHCO3 solution
  5. customdried
  6. concentrationconcentrated to a brown solid
  7. customPurification by HPLC
  8. customgave 0.9 g which
  9. customwas recrystallized from acetone-hexane

Quellen und Nachweise

ORD-Eintrag
ord-29f3638f7aa845eb9e712a515d81e539
Quelldatensatz
uspto-grants-1994_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05324747

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