Ammonium Chloride → (2R,3S)-3-(t-Butoxycarbonylamino)-1-azido-4-cyclohexylbutan-2-ol

HRID 253574

Reaktionsgleichung

Reaktionsgleichung von HRID 253574
[CH:1]1([CH2:7][C@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:9]2[CH2:11][O:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N-:20]=[N+:21]=[N-:22].[Na+].[Cl-].[NH4+]>CO>[C:15]([O:14][C:13]([NH:12][C@@H:8]([CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C@H:9]([OH:10])[CH2:11][N:20]=[N+:21]=[N-:22])=[O:19])([CH3:18])([CH3:17])[CH3:16]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 9816868erythro-N-Boc-L-cyclohexylalanine epoxide

Produkt 1

HCID 14179442(2R,3S)-3-(t-Butoxycarbonylamino)-1-azido-4-cyclohexylbutan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

tert-Butyl (S)-2-cyclohexyl-1-((S)-oxiran-2-yl)ethylcarbamate (492 mg, 1.82 mmol), sodium azide (600 mg, 9.2 mmol), and ammonium chloride (540 mg, 10 mmol) were dissolved in MeOH (26 mL). The reaction was heated to 70° C. for 15 h. The solution was cooled to rt and quenched with water (80 mL). The solution was extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4, and the solvent was removed. The crude (2R,3S)-3-amino-1-azido-4-cyclohexylbutan-2-ol (524 mg) was used without further purification.

Aufarbeitung

  1. temperatureThe solution was cooled to rt
  2. customquenched with water (80 mL)
  3. extractionThe solution was extracted with EtOAc (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed
  7. customThe crude (2R,3S)-3-amino-1-azido-4-cyclohexylbutan-2-ol (524 mg) was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-059767130c084c31a839ee59f8f6d5af
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872028B2

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