Triethylamine → N-{[(1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentyl]carbonyl}-L-valine

HRID 41161

반응식

HRID 41161 반응식
Cl.C[O:3][C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH2:6].[CH3:11][O:12][C@@H:13]1[C@@H:17]([O:18][N+:19]([O-:21])=[O:20])[CH2:16][C@H:15]([C:22](O)=[O:23])[CH2:14]1.C(N(CC)CC)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl>[CH3:11][O:12][C@@H:13]1[C@@H:17]([O:18][N+:19]([O-:21])=[O:20])[CH2:16][C@H:15]([C:22]([NH:6][C@H:5]([C:4]([OH:3])=[O:10])[CH:7]([CH3:9])[CH3:8])=[O:23])[CH2:14]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 111190Methyl valinate hydrochlorideHCID 2724699PyBOPHCID 58443614(1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylic acid

생성물 1

HCID 46220211N-{[(1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentyl]carbonyl}-L-valine수율 90.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of L-valine methyl ester hydrochloride (633 mg, 3.78 mmol), (1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylic acid (755 mg, 3.78 mmol), and triethylamine (1.05 mL, 7.55 mmol) in dichloromethane (30 mL) was added PyBOP (2.95 g, 5.67 mmol). After stirring at rt overnight, the mixture was washed saturated NaHCO3 (3×50 mL) and brine (50 mL), dried over MgSO4, and concentrated. The residue was purified by flash chromatography (RediSepRf 80 g) using 0-40% EtOAc/hexane gradient, affording the title compound (1.04 g, yield 86%): 1H NMR (500 MHz, CDCl3) δ 6.50 (d, J=8.6, 1H), 5.40 (d, J=6.0, 1H), 4.55 (dd, J=4.7, 8.8, 1H), 3.92 (m, 1H), 3.77 (s, 3H), 3.47 (s, 3H), 2.96-2.91 (m, 1H), 2.52-2.46 (m, 1H), 2.38-2.32 (m, 1H), 2.24-2.17 (m, 2H), 2.07-2.01 (m, 1H), 0.97 (d, J=6.9, 3H), 0.92 (d, J=6.9, 3H).

후처리

  1. washthe mixture was washed saturated NaHCO3 (3×50 mL) and brine (50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (RediSepRf 80 g)

출처 및 근거

ORD 기록
ord-90c8cd4faad3491fadd63ecbcc30f34c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530521B2

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