Triethylamine → (1S,2S,4R)-2-methoxy-4-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)cyclopentyl nitrate

HRID 41159

Reaktionsgleichung

Reaktionsgleichung von HRID 41159
[N+:1]([O-:14])([O:3][C@H:4]1[CH2:8][C@H:7]([C:9](=O)[NH2:10])[CH2:6][C@@H:5]1[O:12][CH3:13])=[O:2].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)CC)C.Cl.N[NH:39][C:40]([NH2:42])=[O:41].[OH-].[Na+]>ClCCl>[N+:1]([O-:14])([O:3][C@H:4]1[CH2:8][C@H:7]([C:9]2[NH:42][C:40](=[O:41])[NH:39][N:10]=2)[CH2:6][C@@H:5]1[O:12][CH3:13])=[O:2]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 11236Semicarbazide hydrochlorideHCID 14798Sodium HydroxideHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 58443610(1S,2S,4R)-4-carbamoyl-2-methoxycyclopentyl nitrate

Produkt 1

HCID 136164176(1S,2S,4R)-2-methoxy-4-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)cyclopentyl nitrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(1S,2S,4R)-4-carbamoyl-2-methoxycyclopentyl nitrate (example 14, 0.14 g, 0.68 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (0.19 g, 0.75 mmol) were stirred for 10 minutes in dichloromethane (5 mL) and triethylamine (0.29 mL, 2.1 mmol). Semicarbazide hydrochloride (0.082 g, 0.73 mmol) was added and stirred at room temperature for 4 days. The solution was concentrated in vacuo and brought up in 1 M sodium hydroxide (3 mL, 3.0 mmol) to reflux for 8 hours. Purification of the crude product by reversed-phase mass-directed high-performance liquid chromatography afforded the title compound as a colorless liquid. 1H NMR (500 MHz, CDCl3) δ 1.93-1.98 (m, 1H), 2.34 (dd, J=4.1, 8.3 Hz, 2H), 2.40-2.47 (m, 1H), 2.40-2.47 (m, 1H), 3.42 (quintet, J=6.2 Hz, 1H), 3.50 (s, 3H), 3.93-3.96 (m, 1H), 5.40-5.43 (m, 1H).

Aufarbeitung

  1. concentrationThe solution was concentrated in vacuo
  2. temperatureto reflux for 8 hours
  3. customPurification of the crude product by reversed-phase mass-directed high-performance liquid chromatography

Quellen und Nachweise

ORD-Eintrag
ord-22e3c288424f496b8bb664fc6edef27d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530521B2

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