Boron trifluoride etherate → (2S,3S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoate

HRID 523177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 523177
[CH2:1]([C@H:3]1[N:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[C@@H:4]1[C:13]([O:15][CH3:16])=[O:14])[CH3:2].[CH3:17][C@@H:18]([OH:23])[CH2:19][CH2:20][CH:21]=[CH2:22].B(F)(F)F.O(CC)CC>C(Cl)Cl>[C:9]([O:8][C:6]([NH:5][C@@H:4]([C@@H:3]([O:23][C@@H:18]([CH2:19][CH2:20][CH:21]=[CH2:22])[CH3:17])[CH2:1][CH3:2])[C:13]([O:15][CH3:16])=[O:14])=[O:7])([CH3:12])([CH3:11])[CH3:10]

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 11848709(2R)-hex-5-en-2-olHCID 90118291(2S,3R)-1-tert-butyl 2-methyl 3-ethylaziridine-1,2-dicarboxylate

Produkt 1

HCID 90118054(2S,3S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoateAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a round-bottom flask equipped with a stir bar was added (2S,3R)-1-tert-butyl 2-methyl 3-ethylaziridine-1,2-dicarboxylate (691, 3.02 mmol) and CH2Cl2 (12 mL). To the solution was added (R)-hex-5-en-2-ol (363 mg, 3.62 mmol), then BF3-OEt2 (1.0M in CH2Cl2, 0.30 mL). The solution was stirred at room temperature for 16 h. The solution was transfered to a separatory funnel and was diluted with CH2Cl2, then the solution was washed with aq. saturated NaHCO3; then brine. The organic phase was dried over Na2SO4; filtered; then concentrated in vacuo. The resulting residue was subjected to silica gel chromatography (hexanes:EtOAc 90:10 to 70:30) to afford (2S,3S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoate as a colorless oil (426 mg, 43%). 1H-NMR (500 MHz, CDCl3) δ 5.81 (ddt, J=17.0, 10.4, 6.5 Hz, 1H), 5.19 (d, J=7.7 Hz, 1H), 5.08-5.00 (m, 1H), 4.96 (dd, J=10.2, 1.7 Hz, 1H), 4.50 (dd, J=8.3, 3.5 Hz, 1H), 3.75 (s, 3H), 3.65-3.58 (m, 1H), 3.57-3.50 (m, 1H), 2.19-2.06 (m, 2H), 1.66-1.56 (m, 2H), 1.55-1.38 (m, 11H), 1.13 (d, J=6.1 Hz, 3H), 0.97 (t, J=7.3 Hz, 3H).

Aufarbeitung

  1. customTo a round-bottom flask equipped with a stir bar
  2. customThe solution was transfered to a separatory funnel
  3. washthe solution was washed with aq. saturated NaHCO3
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthen concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a1e30f0bc4904477b629e6498707bb29
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334279B2

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