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

HRID 41159

反応式

HRID 41159 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-22e3c288424f496b8bb664fc6edef27d
出典データセット
uspto-grants-2013_09
特許番号
US08530521B2

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