Methanol → N6-Trityl-Lysine

HRID 1836947

Reaktionsgleichung

Reaktionsgleichung von HRID 1836947
Cl.Cl.[NH2:3][C@H:4]([C:10]([OH:12])=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8][NH2:9].C(N(CC)CC)C.[C:20]1([C:26](Cl)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CO>ClCCl>[C:26]([NH:9][CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]([C:10]([OH:12])=[O:11])[NH2:3])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 6456Trityl chloride2×HCID 8471TriethylamineHCID 69567Lysine dihydrochloride

Produkt 1

HCID 13943552N6-Trityl-LysineAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Lysine 2HCL (1.012 g, 4.34 mmol) was suspended in 300 ml dichloromethane, and sonicated until suspension was homogeneous. Triethylamine (7.5 ml, 54.1 mmol, 2.5 eq.) was added and the mixture was left to stir for 20 minutes in Brine/Ice bath (−15° C). Triphenylmethylchloride (Trityl chloride) (6.00 g, 21.5 mmol, 1 eq.) was dissolved in 200 ml dichloromethane and then slowly added over a period of 1 hour via a dropping funnel to the reaction flask. The reaction was followed by TLC (Silica, 5% methanol/95% CH2Cl2) and was stopped 1 hour after disappearance of Trityl chloride. Volume was reduced by reduced pressure distillation. The reaction product was washed first with 5% sodium bicarbonate (2×, 20 ml each), brine (1×, 20 ml), dried over sodium sulfate, filtered, and the solvent removed at reduced pressure distillation. The product was purified by flash column chromatography (Silica Gel, 3% methanol/97% CH2Cl2) and isolated as a clear golden oil (0.753 g. Yield: 43%). 1H NMR (CDCl3, 300 MHz δ1.40 (m, 2H), 1.52 (m, 2H), 1.67 (m, 2H), 2.11 (t,2H), 3.41 (t, 1H), 3.69 (s,3H), 7.14-7.51 (m, 15H); 13C NMR (CDCl3, 75 MHz) δ23.6, 30.7, 35.0, 43.5, 51.9, 54.5, 71.0, 126.2, 127.8, 128.7, 146.4, 176.6; ESI-MS calculated for C27H30N2O2 402.53; found 403.6 [M++1].

Aufarbeitung

  1. customsonicated until suspension
  2. waitthe mixture was left
  3. additionslowly added over a period of 1 hour via a dropping funnel to the reaction flask
  4. distillationVolume was reduced by reduced pressure distillation
  5. washThe reaction product was washed first with 5% sodium bicarbonate (2×, 20 ml each), brine (1×, 20 ml)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed at reduced pressure distillation
  9. customThe product was purified by flash column chromatography (Silica Gel, 3% methanol/97% CH2Cl2)
  10. customisolated as a clear golden oil (0.753 g. Yield: 43%)

Quellen und Nachweise

ORD-Eintrag
ord-c3ab0a6ec7ba4a3c9b3987c19bb7ba76
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06780856B2

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