Water → 2,2-dimethoxyethyl N-benzyloxycarbonylglycine

HRID 39248

Reaktionsgleichung

Reaktionsgleichung von HRID 39248
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=[O:14])=[O:10])=[CH:3][CH:2]=1.[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19]Br.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19][N:11]([C:9]([O:8][CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)=[O:10])[CH2:12][C:13]([OH:15])=[O:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 14349BenzyloxycarbonylglycineHCID 816722-Bromo-1,1-dimethoxyethane

Produkt 1

HCID 671854852,2-dimethoxyethyl N-benzyloxycarbonylglycineAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of N-α-CBZ-glycine (2.0 g, 9.57 mmol), bromoacetaldehyde dimethyl acetal (2.25 mL, 19.13 mmol) and Cs2CO3 (2.78 g, 3.12 mmol) in 20 mL of anhydrous DMF was stirred at 100° C. for 24 h. After cooling to room temperature, water was added and the mixture was extracted with ethyl acetate (3×80 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using 45-50% ethyl acetate/hexanes to give the product 37 (1.74 g, 61%). 1H NMR (400 MHz, CDCl3) δ 3.38 (s, 6H), 3.98 (d, J=5.7 Hz, 2H), 4.12 (d, J=5.3 Hz, 2H), 4.54 (t, J=5.3 Hz, 1H), 5.10 (s, 2H), 5.50 (bs, 1H), 7.32 (m, 5H).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with ethyl acetate (3×80 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel using 45-50% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c1c0015e7ace4502a20afd5e8a5bf10e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524691B2

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