Benzyl Bromide → methyl O-benzyl-N-trityl-L-serinate

HRID 221568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 221568
[C:1]([NH:20][C@H:21]([C:24]([O:26][CH3:27])=[O:25])[CH2:22][OH:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1>[CH2:30]([O:23][CH2:22][C@@H:21]([C:24]([O:26][CH3:27])=[O:25])[NH:20][C:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 7128367N-(Triphenylmethyl)-L-serine methyl ester

Produkt 1

HCID 67156483methyl O-benzyl-N-trityl-L-serinateAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5963Benzyltrimethylammonium chlorideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Methyl N-trityl-L-serinate (3.61 g, 10.0 mmol), prepared by the method of Baldwin, Tetrahedron, 49, pp. 6309-6330, (1993), was dissolved in 50 mL of CH2Cl2 followed by the addition of 25 mL of 50% aqueous NaOH solution. To the stirred mixture were added benzyltrimethylammonium chloride (186 mg, 1.00 mmol) and benzyl bromide (1.20 mL, 10.0 mmol). After stirring overnight, the mixture was treated with 100 mL of ice water. After all of the ice had melted, 100 mL of CH2Cl2 was added and the layers were separated. The aqueous portion was extracted with another 50 mL of CH2Cl2 and the combined organic layers were washed with H2O (2×100 mL) and brine (3×50 mL). The organic portion was dried over Na2SO4, filtered and concentrated. Chromatography (SiO2, 10-20% ethyl acetate/hexanes) gave 3.22 g of methyl O-benzyl-N-trityl-L-serinate as a colorless syrup.

Aufarbeitung

  1. customthe layers were separated
  2. extractionThe aqueous portion was extracted with another 50 mL of CH2Cl2
  3. washthe combined organic layers were washed with H2O (2×100 mL) and brine (3×50 mL)
  4. dry with materialThe organic portion was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c1e2f3844de94f07a86afb60db67a172
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207162B2

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