Triethylamine → (R)-tert-Butyl 1-azido-3-methoxypropan-2-ylcarbamate

HRID 2092843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2092843
CS(Cl)(=O)=O.O[CH2:7][C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9][O:10][CH3:11].CCN(CC)CC.[N-:27]=[N+:28]=[N-:29].[Na+]>C(Cl)Cl.CCOC(C)=O>[N:27]([CH2:7][C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9][O:10][CH3:11])=[N+:28]=[N-:29]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 15287812N-Boc-(R)-2-amino-3-methoxy-1-propanol

Produkt 1

HCID 86654731(R)-tert-Butyl 1-azido-3-methoxypropan-2-ylcarbamateAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methanesulfonyl chloride (4.0 g, 35 mmol) in DCM (50 mL) was slowly added to a solution of (R)-tert-butyl 1-hydroxy-3-methoxypropan-2-ylcarbamate (6.0 g, 29 mmol) and Et3N (3.64 g, 36 mmol) in DCM (150 mL) at 0° C. The reaction mixture was stirred at RT for 2 h. The organic phase was washed with water and saturated aq NaHCO3, concentrated, and dissolved in DMF. Sodium azide (2.34 g, 36.0 mmol) was added, and the reaction mixture was stirred at 75° C. for 4 h. The reaction mixture was diluted by EtOAc and washed with water. The crude product was purified by column chromatography on silica gel eluting with EtOAc and petroleum ether (EtOAc/PE=2/1) to give the title compound (4.3 g, 64%). 1H NMR (400 MHz, CDCl3) δ ppm 4.92 (s, 1H), 3.91 (m, 1H), 3.53-3.48 (m, 2H), 3.45-3.40 (m, 2H), 3.38 (s, 3H), 1.47 (s, 9H).

Aufarbeitung

  1. washThe organic phase was washed with water and saturated aq NaHCO3
  2. concentrationconcentrated
  3. dissolutiondissolved in DMF
  4. stirringthe reaction mixture was stirred at 75° C. for 4 h
  5. washwashed with water
  6. customThe crude product was purified by column chromatography on silica gel eluting with EtOAc and petroleum ether (EtOAc/PE=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-957e41c2208c48dbb45b3af3015c8fc2
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440689B2

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