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 1861254

반응식

HRID 1861254 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3155e3f9dcbf4d94a261c7938d49d465
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06531474B1

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