Ethyl Acetate → 2-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-N-indan-1-yl-2-phenyl-acetamide

HRID 48571

반응식

HRID 48571 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=2)CCC1C1(CC(O)=O)C=CC=CC1.C1CN([P+](ON2N=N[C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][C:54]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:69][CH:70]1[C:78]2[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=2)[CH2:72][CH2:71]1.[CH:79](N(C(C)C)CC)([CH3:81])[CH3:80].CCO[C:91]([CH3:93])=[O:92]>CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=2)[CH2:81][CH2:79][CH:80]1[CH:93]([C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)[C:91]([NH:69][CH:70]1[C:78]2[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=2)[CH2:72][CH2:71]1)=[O:92]

참가 물질

8

반응물 5

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 123445(+-)-1-AminoindanHCID 2724699PyBOPHCID 697588751-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-phenyl-acetic acid

생성물 1

HCID 227428352-[1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-N-indan-1-yl-2-phenyl-acetamide수율 64%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-phenyl-acetic acid (100 mg, 0.209 mmol) in 5 ml of dry DMF, were added PyBOP (109 mg, 0.209 mmol), 1-aminoindane (32.3 mg, 0.19 mmol) and dropwise diisopropylethylamine (Hünig's base). (75 μl, 0.437 mmol). The mixture reaction was stirred at RT under argon for 20 h. The mixture was then dissolved in CH2Cl2 and washed with water. The aqueous phase was extracted twice with CH2Cl2, the combined organic extracts were dried over MgSO4, filtered and concentrated to give a crude brown residue. Flash chromatography (AcOEt) gave 72 mg (64%) of the title compound as a pale brown oil.

후처리

  1. customThe mixture reaction
  2. washwashed with water
  3. extractionThe aqueous phase was extracted twice with CH2Cl2
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude brown residue

출처 및 근거

ORD 기록
ord-527294e8a58b45c3b7dcceae1de8be76
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703392B2

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