Water → HCID 59486012、化合物

HRID 1972195ノート

反応式

HRID 1972195 の反応式
[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]

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 61277Isopropyl isocyanateHCID 24946196HCID 24946196、化合物

生成物 1

HCID 59486012HCID 59486012、化合物収率 33.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-3d27a7fc1c234dac8990102c1245eb8e
出典データセット
uspto-grants-2013_04
特許番号
US08431607B2

反応ノート

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