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

HRID 41159

반응식

HRID 41159 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-22e3c288424f496b8bb664fc6edef27d
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530521B2

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