7,12-Dimethylbenz(a)anthracene → 1-[2-(3,5-Dichloro-4-hydroxy-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amide

HRID 900575

反応式

HRID 900575 の反応式
[CH2:1]([O:8][CH:9]1[CH:13]([NH:14][C:15]([CH:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22](=[O:40])[CH:23]([NH:25][C:26](=[O:39])[C:27]2[CH:32]=[C:31]([Cl:33])[C:30]([O:34]CC=C)=[C:29]([Cl:38])[CH:28]=2)[CH3:24])=[O:16])[CH2:12][C:11](=[O:41])[O:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C2C(=CC=CC=2)C(C)=C2C=1C=CC1C2=CC=CC=1>C(Cl)Cl.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>[CH2:1]([O:8][CH:9]1[CH:13]([NH:14][C:15]([CH:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22](=[O:40])[CH:23]([NH:25][C:26](=[O:39])[C:27]2[CH:32]=[C:31]([Cl:33])[C:30]([OH:34])=[C:29]([Cl:38])[CH:28]=2)[CH3:24])=[O:16])[CH2:12][C:11](=[O:41])[O:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 60017,12-Dimethylbenz(a)anthraceneHCID 229774861-[2-(4-Allyloxy-3,5-dichloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amide

生成物 1

HCID 229777651-[2-(3,5-Dichloro-4-hydroxy-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-benzyloxy-5-oxo-tetrahydro-furan-3-yl)-amide収率 71.8%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A 140 mg sample of 82 (0.23 mmol) was dissolved in CH2Cl2 (4 mL) and treated with DMBA (35.4 mg, 0.26 mmol) and Pd(PPh3)4 (32 mg, 0.028 mmol). The solution was stirred at 0° C. for 15 mins, warmed to room temperature for 2 hours, then diluted with CH2Cl2 and washed with water (2×) and brine. The solvent was concentrated in vacuo and the residue purified by flash chromatography on silica gel using MeOH/CH2Cl2 (1/99 to 3/97) to give the title compound (93.2 mg, 71% yield). 1H-NMR (500 MHz, CD3OD) δ 1.16 (d, 0.25H), 1.28-1.49 (m, 2.75H), 1.63-2.33 (m, 4H), 2.48 (dd, 0.4H), 3.39-3.59 (m, 0.2H), 3.60-3.73 (m, 0.8H), 3.73-3.96 (m, 1H), 4.24-4.48 (m, 2H), 4.57-4.92 (m, 7H), 5.44 (s, 0.4H), 5.50 (d, 0.4H), 5.64 (d, 0.8H), 5.75 (d, 0.5H), 7.16-7.43 (m, 5H), 7.78-7.89 (m, 1.6H), 8.40-8.63 (m, 0.4H). Analytical HPLC (cyano column) (mixture of 2 diastereomers) 11.57, 11.82 min. LC-MS (ES+) m/e=564.1 (M+H).

後処理

  1. temperaturewarmed to room temperature for 2 hours
  2. washwashed with water (2×) and brine
  3. concentrationThe solvent was concentrated in vacuo
  4. customthe residue purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-55c36cc1aefe4e01b4b6ea0432922684
出典データセット
uspto-grants-2008_04
特許番号
US07358273B2

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