Ammonium Chloride → tert-Butyl-(1S,2R)-3-azido-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate

HRID 14009

Reaktionsgleichung

Reaktionsgleichung von HRID 14009
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].[F:7][C:8]1[CH:9]=[C:10]([CH2:15][C@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C@H:17]2[CH2:19][O:18]2)[CH:11]=[C:12]([F:14])[CH:13]=1>>[C:23]([O:22][C:21](=[O:27])[NH:20][C@@H:16]([CH2:15][C:10]1[CH:9]=[C:8]([F:7])[CH:13]=[C:12]([F:14])[CH:11]=1)[C@H:17]([OH:18])[CH2:19][N:1]=[N+:2]=[N-:3])([CH3:24])([CH3:25])[CH3:26]

Komponenten

4

Edukt 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 9922319tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamate

Produkt 1

HCID 131726251tert-Butyl-(1S,2R)-3-azido-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate

Reaktionsbedingungen

Temperatur
77.5 °C

Versuchsvorschrift

Sodium azide (0.22 g, 4 mmole) and ammonium chloride (2 eq) are added to tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V, EXAMPLE 3, 0.6 g, 2 mmole). The reaction is heated to 75-80 degrees C. and stirred for 16 hours. The reaction is monitored by TLC to insure completion. The solvent is removed under reduced pressure. The concentrate is partitioned between ethyl acetate and water, the phases are separated and the organic phase is washed with bicarbonate and saline, dried over anhydrous sodium sulfate and concentrated to give the title compound, TLC (ethyl acetate/hexane) Rf=0.45; MS (MH+)=343.

Aufarbeitung

  1. customThe solvent is removed under reduced pressure
  2. customThe concentrate is partitioned between ethyl acetate and water
  3. customthe phases are separated
  4. washthe organic phase is washed with bicarbonate and saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3265c8a9ae9c4080b431247124a255c4
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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