Water → HCID 59486012, 화합물

HRID 1972195노트

반응식

HRID 1972195 반응식
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C@H:16]([CH2:24][OH:25])[O:15][C:14]3=[O:26])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH:29]([N:32]=[C:33]=[O:34])([CH3:31])[CH3:30].O.C(OCC)(=O)C>CN(C=O)C>[CH:29]([NH:32][C:33](=[O:34])[O:25][CH2:24][C@@H:16]1[O:15][C:14](=[O:26])[N:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:28][CH:27]=3)=[CH:12][CH:11]=2)[C@H:17]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:31])[CH3:30]

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 61277Isopropyl isocyanateHCID 24946196HCID 24946196, 화합물

생성물 1

HCID 59486012HCID 59486012, 화합물수율 33.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To (4S,5R)-3-(4-(4-chlorophenoxy)phenyl)-5-(hydroxymethyl)-4-phenyloxazolidin-2-one (33 mg, 0.08 mmol) in 0.3 mL DMF was added isopropyl isocyanate (0.015 mL, 0.16 mmol). The reaction was stirred for 3 h at room temperature until reaction completed as judged by TLC. Water and ethyl acetate were added and the phases separated. The organic phase was washed with brine, dried (MgSO4), and concentrated. 13 mg (33%) of the title compound was obtained as a white solid after Prep-LC purification (10-90 Acetonitrile/water (0.05% ammonium acetate). 1H NMR (CDCl3) δ (ppm) 7.30-7.39 (m, 7H), 7.23-7.26 (m, 2H), 6.84-6.90 (m, 4H), 5.14 (d, 1H, J=5.6 Hz), 4.67 (d, 1H, J=7.2 Hz), 4.34-4.53 (m, 3H), 3.77-3.85 (m, 1H), 1.17 (d, 3H, J=6.5 Hz), 1.13 (d. 3H, J=6.5 Hz). HPLC-MS calculated C26H25ClN2O5 (M+H+): 481.2, found: 481.1.

후처리

  1. customthe phases separated
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3d27a7fc1c234dac8990102c1245eb8e
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431607B2

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