1,2-Dichloroethane → HCID 9892498、化合物

HRID 2220109ノート

反応式

HRID 2220109 の反応式
C[N:2]1[C:9](=O)[CH2:8][C:6](=[O:7])N(C)C1=O.[NH2:12][C:13]1[CH:36]=[CH:35][C:16]([C:17]([NH:19][CH:20]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:21]([N:23]2[CH2:27][CH2:26][CH2:25][CH:24]2[C:28](O)=[O:29])=[O:22])=[O:18])=[CH:15][C:14]=1[Cl:37].C(N(C(C)C)CC)(C)C.C(Cl)CCl.[CH3:51][CH2:52][O:53][C:54](C)=[O:55]>C(Cl)Cl.CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:52]([O:53][CH:54]1[CH:9]([NH:2][C:28]([CH:24]2[CH2:25][CH2:26][CH2:27][N:23]2[C:21](=[O:22])[CH:20]([NH:19][C:17](=[O:18])[C:16]2[CH:35]=[CH:36][C:13]([NH2:12])=[C:14]([Cl:37])[CH:15]=2)[C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:8][C:6](=[O:7])[O:55]1)[CH3:51]

参加物

9

反応物 5

HCID 111,2-DichloroethaneHCID 8857Ethyl AcetateHCID 69860Dimethylbarbituric acidHCID 81531DiisopropylethylamineHCID 10156704VX-765

生成物 1

HCID 9892498HCID 9892498、化合物収率 77%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 6 (5.05 g, 22.0 mmol) in CH2Cl2 (50 mL) at 0° C. was added 1,3-dimethylbarbituric acid (DMBA) (3.78 g, 24.2 mmol)and Pd(PPh3)4 (0.15 g, 0.13 mmol) After 10 minutes, a solution of 5 (8.40 g, 22.0 mmol) in DMF (25 mL) was added followed by diisopropylethylamine (DIPEA) (7.66 mL, 44.1 mmol), (2.98 g, 22.0 mmol) and EDC (5.06 g, 26.4 mmol). The solution was stirred at 0° C. for 10 minutes then at room temperature for 18 hours. The reaction was diluted with EtOAc (200 mL), washed with 0.5N NaHSO4 (2×200 mL), 10% NaHCO3 (2×200 mL), saturated NaCl (1×150 mL), dried over anhydrous MgSO4, and evaporated to dryness. Flash column chromatography on silica gel using CH2Cl2/MeOH, (99/1 to 98/2%) afforded the title compound as a white solid (11.20 g, 77% yield): 1H-NMR (500 MHz, CDCl3) δ1.08 (s, 9H), 1.27 (t, 3H), 1.85–1.99 (m, 1H), 2.00–2.06 (m. 1H), 2.07–2.18 (m, 1H), 2.32–2.48 (m, 2H), 2.78–2.89 (m, 1H), 3.62–3.76 (m, 2H), 3.82–3.96 (m, 2H), 4.39 (s, 1H), 4.54–4.60 (m, 1H), 4.62–4.76 (m, 1H), 4.85 (d, 1H), 6.57 (d, 1H), 6.73 (d, 1H), 7.38 (d, 1H), 7.49 (d, 1H), 7.72 (s, 1H). Analytical HPLC (cyano column): 13.10 min. LC-MS (ES+) m/e=509.4 (M+H), m.p.=96–99 ° C.

後処理

  1. waitat room temperature for 18 hours
  2. washwashed with 0.5N NaHSO4 (2×200 mL), 10% NaHCO3 (2×200 mL), saturated NaCl (1×150 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated to dryness

出典と根拠

ORDレコード
ord-d36a7cd1659745388ba6f7a58aa52967
出典データセット
uspto-grants-2008_08
特許番号
US07417029B2

反応ノート

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