Water → Methyl-(s)-1-[(s)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl-amino]-1-oxo-3-phenylpropan-2-ylcarbamate

HRID 2382236Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2382236
[CH2:1]([C:3]1[N:4]=[C:5]([C@@H:8]([NH:19][C:20](=[O:37])[C@@H:21]([NH:29][C:30](=[O:36])[O:31][C:32](C)(C)C)[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[S:6][CH:7]=1)[CH3:2].ClC(OC)=O.O>Cl.O1CCOCC1>[CH3:32][O:31][C:30](=[O:36])[NH:29][C@@H:21]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:20]([NH:19][C@H:8]([C:5]1[S:6][CH:7]=[C:3]([CH2:1][CH3:2])[N:4]=1)[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=1)=[O:37]

Komponenten

6

Edukt 3

HCID 962WaterHCID 6586Methyl chloroformateHCID 57943172Tert-butyl (5)-1-[(5)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethylamino]-1-oxo-3-phenylpropan-2-ylcarbamate

Produkt 1

HCID 57943180Methyl-(s)-1-[(s)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl-amino]-1-oxo-3-phenylpropan-2-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

tert-butyl (S)-1-[(S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethylamino]-1-oxo-3-phenylpropan-2-ylcarbamate, 8, (0.460 mg, 0.881 mmol) is dissolved in a solution of 4M hydrogen chloride in 1,4-dioxane (4 mL). The reaction mixture is stirred 1 hour, and the solvent is removed under reduced pressure. The resulting crude amine is dissolved in CHCl3 (8 mL) and pyridine (1 mL) is added. The temperature is cooled to 0° C. and methyl chloroformate (0.083 g, 0.881 mmol) is added dropwise. The reaction mixture is allowed to warm to room temperature and stirred for 2 days. Water is added, the solution stirred for 15 minutes and then extracted several times with CHCl3. The combined organic layers are washed with 1N HCl, 5% NaHCO3, and brine, dried over Na2SO4, and filtered. The solvent is removed in vacuo to afford 0.297 g of the desired product.

Aufarbeitung

  1. customthe solvent is removed under reduced pressure
  2. dissolutionThe resulting crude amine is dissolved in CHCl3 (8 mL)
  3. additionpyridine (1 mL) is added
  4. temperatureto warm to room temperature
  5. stirringstirred for 2 days
  6. stirringthe solution stirred for 15 minutes
  7. extractionextracted several times with CHCl3
  8. washThe combined organic layers are washed with 1N HCl, 5% NaHCO3, and brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customThe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-45b4f1e91bc04c088f12654bc396e231
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258311B2

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