Methyl iodide → N2 [(1,1-Dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine, methyl ester

HRID 264969

Reaktionsgleichung

Reaktionsgleichung von HRID 264969
[C:1](=O)([O-])[O-].[Cs+].[Cs+].[N:7]#[N:8].[CH3:9][C:10]([CH3:35])([O:12][C:13]([NH:15][C@H:16]([C:32]([OH:34])=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])=[O:14])[CH3:11].O.CO.CI>C(OCC)(=O)C.O>[N:7]#[N:8].[CH3:11][C:10]([CH3:35])([O:12][C:13]([NH:15][C@H:16]([C:32]([O:34][CH3:1])=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])=[O:14])[CH3:9]

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 22242641Methanol--water (1/1)HCID 86742311N2 [(1,1-dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine

Produkt 1

HCID 131714291N2 [(1,1-Dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

Cesium carbonate (4.28 g., 13.1 mmoles) was added to a mixture of N2 -[(1,1-dimethylethoxy)carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysine (10 g., 26.3 mmoles) and 20% water-methanol (60 ml.). The solution became homogeneous within 5 minutes so the solvent was stripped add the residual water removed azeotropically with acetonitrile (3x). The resulting oil was dried in vacuo, dissolved in dry dimethyl-formamide and treated with methyl iodide (3.2 ml., 2.0 eq.). The reaction mixture was stirred at room temperature for 1.5 hours under argon, diluted with ethyl acetate (200 ml.) and washed successively with water (2×25 ml.), saturated sodium bicarbonate (25 ml.) and brine (25 ml.). The organic phase was dried (anhydrous magnesium sulfate), filtered, evaporated to dryness and dried in vacuo to give 10.11 g., of product as a light yellow syrup; Rf =0.30 (ethyl acetate:hexanes, 1:2).

Aufarbeitung

  1. customremoved azeotropically with acetonitrile (3x)
  2. customThe resulting oil was dried in vacuo
  3. dissolutiondissolved in dry dimethyl-formamide
  4. washwashed successively with water (2×25 ml.), saturated sodium bicarbonate (25 ml.) and brine (25 ml.)
  5. dry with materialThe organic phase was dried (anhydrous magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customdried in vacuo
  9. customto give 10.11 g

Quellen und Nachweise

ORD-Eintrag
ord-7981a249e7574dbd9f027cf3a3a39db0
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646276

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