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Sodium Azide → 17-(2-((5-Azidopentyl)oxy)acetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

HRID 2039395
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2039395
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH2:8][C:9]([CH:11]1[C:27]2([CH3:28])[CH:14]([CH:15]3[CH:24]([CH2:25][CH2:26]2)[C:23]2([CH3:29])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)=[O:10].[N-:31]=[N+:32]=[N-:33].[Na+]>CN(C)C=O>[N:31]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH2:8][C:9]([CH:11]1[C:27]2([CH3:28])[CH:14]([CH:15]3[CH:24]([CH2:25][CH2:26]2)[C:23]2([CH3:29])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)=[O:10])=[N+:32]=[N-:33]
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Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 8667556417-(2-((5-Bromopentyl)oxy)acetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

Produkt 1

HCID 7118308317-(2-((5-Azidopentyl)oxy)acetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-oneAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of 7 (125 mg, 0.261 mmol) in anhydrous N,N-dimethylformamide (7 mL) was added sodium azide (169 mg, 2.61 mmol). The reaction mixture was heated to 65° C. and stirred overnight. Excess sodium azide was filtered off and the solvent was removed by rotary evaporation. The crude residue was dissolved in ethyl acetate and washed with water three times. The organic layer was dried over sodium sulfate and concentrated followed by flash chromatography in hexanes/ethyl acetate (2:1) to give 9 (78 mg, 68%). 1H NMR (500 MHz, CD3OD) δ 5.61 (d, J=4.9 Hz, 1H), 3.39 (t, J=6.4 Hz, 2H), 3.25-3.17 (m, 4H), 2.60 (t, J=9.1 Hz, 1H), 2.45-2.33 (m, 2H), 2.25-2.15 (m, 2H), 2.12-2.03 (m, 1H), 1.99 (m, 1H), 1.89-1.76 (m, 2H), 1.70-1.29 (m, 15H), 1.29-1.15 (m, 2H), 1.13 (d, J=11.0 Hz, 4H), 1.04-0.87 (m, 2H), 0.60 (s, 3H). 13C NMR (125 MHz, CD3OD) δ 210.81, 202.29, 174.92, 124.24, 78.00, 72.34, 62.71, 59.71, 57.39, 55.16, 52.43, 45.67, 39.99, 39.72, 36.81, 34.72, 33.90, 33.20, 30.15, 29.75, 25.52, 24.46, 24.17, 23.76, 22.15, 17.67, 13.96. ESI-MS m/z [M+Na]+ observed: 464.2, calculated: 464.3.

Aufarbeitung

  1. filtrationExcess sodium azide was filtered off
  2. customthe solvent was removed by rotary evaporation
  3. dissolutionThe crude residue was dissolved in ethyl acetate
  4. washwashed with water three times
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d2b7005f53774e9db978ec53c7fc41cb
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08580231B2

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