Ammonium Chloride → benzyl [(1S)-1-methyl-2-(1-methyl-1H-imidazol-4-yl)-2-oxoethyl]carbamate

HRID 1028606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1028606
CON(C)[C:4](=[O:18])[C@@H:5]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:6].C([Mg]Cl)(C)C.C([Mg]Br)C.I[C:30]1[N:31]=[CH:32][N:33]([CH3:35])[CH:34]=1.[NH4+].[Cl-]>C(Cl)Cl.C1COCC1.CCOCC.O>[CH3:6][C@H:5]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:4]([C:30]1[N:31]=[CH:32][N:33]([CH3:35])[CH:34]=1)=[O:18]

Komponenten

10

Edukt 5

HCID 25517Ammonium ChlorideHCID 27734634-Iodo-1-methyl-1H-imidazoleHCID 10515879(S)-Benzyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamateHCID 178418443HCID 178418443, VerbindungHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 59135236benzyl [(1S)-1-methyl-2-(1-methyl-1H-imidazol-4-yl)-2-oxoethyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A solution of benzyl {(1S)-2-[methoxy(methyl)amino]-1-methyl-2-oxoethyl}carbamate (64 mg, 0.24 mmol) in CH2Cl2 (1 mL) was cooled to −20° C. under N2, and isopropylmagnesium chloride (120 μL of a 2.0 M solution in THF) was added dropwise. The mixture was stirred at −20° C. for 20 min. In a separate flask ethylmagnesium bromide (480 μL of a 2.0 M solution in Et2O) was added to a solution of 4-iodo-1-methyl-1-H-imidazole (109 mg, 0.48 mmol) in dry CH2Cl2 (1.5 mL) at room temperature. The resulting mixture was stirred for 20 min and then added by cannula to the solution above slowly. The resulting solution was left to stir overnight. Saturated NH4Cl was added to the reaction solution. The mixture was diluted with water and the aqueous phase was extracted with CH2Cl2 (2×25 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. Flash chromatography of the residue yielded benzyl [(1S)-1-methyl-2-(1-methyl-1H-imidazol-4-yl)-2-oxoethyl]carbamate. LCMS calc.=288.14; found=288.3 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 7.65 (s, 1 H); 7.47 (s, 1 H); 7.35-7.28 (m, 5 H); 5.93 (d, J=6.9 Hz, 1 H); 5.29-5.25 (m, 1 H); 5.13 (s, 2 H); 3.73 (s, 3 H); 1.26 (d, J=7.1 Hz, 3H).

Aufarbeitung

  1. stirringThe resulting mixture was stirred for 20 min
  2. additionadded by cannula to the solution above slowly
  3. waitThe resulting solution was left
  4. stirringto stir overnight
  5. extractionthe aqueous phase was extracted with CH2Cl2 (2×25 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d48572216fa64795b16ba52f245c6547
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735435B2

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