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

HRID 900630

반응식

HRID 900630 반응식
[CH2:1]([O:3][CH:4]1[CH:8]([NH:9][C:10]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17](=[O:35])[CH:18]([NH:20][C:21](=[O:34])[C:22]2[CH:27]=[C:26]([Cl:28])[C:25]([O:29]CC=C)=[C:24]([Cl:33])[CH:23]=2)[CH3:19])=[O:11])[CH2:7][C:6](=[O:36])[O:5]1)[CH3:2].CC1C2C(=CC=CC=2)C(C)=C2C=1C=CC1C2=CC=CC=1.C(Cl)Cl.CO>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:3][CH:4]1[CH:8]([NH:9][C:10]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17](=[O:35])[CH:18]([NH:20][C:21](=[O:34])[C:22]2[CH:23]=[C:24]([Cl:33])[C:25]([OH:29])=[C:26]([Cl:28])[CH:27]=2)[CH3:19])=[O:11])[CH2:7][C:6](=[O:36])[O:5]1)[CH3:2]

참가 물질

6

반응물 3

HCID 60017,12-Dimethylbenz(a)anthraceneHCID 21226129Dichloromethane methanolHCID 229774871-[2-(4-Allyloxy-3,5-dichloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide

생성물 1

HCID 229774631-[2-(3,5-Dichloro-4-hydroxy-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide수율 77%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 110 (194 mg, 0.36 mmol) in CH2Cl2 (5 ml) was added DMBA (70.7 mg, 0.45 mmol) and Pd(PPh3)4 (50.3 mg, 0.044 mmol) at 0° C. The solution was warmed to room temperature after 15 mins, stirred for 2 hours, diluted with CH2Cl2 then washed with water (2×) and brine. The organic layer was dried over anhydrous Na2SO4 and evaporated to give the crude product. Flash chromatography using CH2Cl2/MeOH (99/1 to 95/5%) afforded the title compound (138.6 mg, 77% yield). 1H-NMR (500 MHz, CD3OD) δ 1.13-1.31 (m, 3H), 1.35-1.49 (m, 3H), 1.84-2.35 (m, 4H), 2.43-3.05 (m, 2H), 3.48-3.93 (m, 4H), 4.22-4.80 (m, 3H), 5.38 (d, 0.4H), 5.46 (s, 0.1H), 5.55-5.61 (m, 0.5H), 7.76-7.94 (m, 2H). Analytical HPLC 8.70 min. LC-MS (ES+) m/e=502.2 (MH+).

후처리

  1. washthen washed with water (2×) and brine
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. customevaporated
  4. customto give the crude product

출처 및 근거

ORD 기록
ord-94526c3344014c169f5acc6f84249861
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07358273B2

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