Benzyl 3-(2-ethoxy-2-oxoethyl)-3-(3-(4-octylphenyl)ureido)pyrrolidine-1-carboxylate → Ethyl 2-(3-(3-(4-octylphenyl)ureido)pyrrolidin-3-yl)acetate

HRID 1192902노트

반응식

HRID 1192902 반응식
[CH2:1]([O:3][C:4](=[O:39])[CH2:5][C:6]1([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:27][CH:26]=2)=[O:23])[CH2:10][CH2:9][N:8](C(OCC2C=CC=CC=2)=O)[CH2:7]1)[CH3:2]>CCO.[Pd]>[CH2:31]([C:28]1[CH:27]=[CH:26][C:25]([NH:24][C:22](=[O:23])[NH:21][C:6]2([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:39])[CH2:10][CH2:9][NH:8][CH2:7]2)=[CH:30][CH:29]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

참가 물질

4

반응물 1

HCID 66865221Benzyl 3-(2-ethoxy-2-oxoethyl)-3-(3-(4-octylphenyl)ureido)pyrrolidine-1-carboxylate

생성물 1

HCID 66865457Ethyl 2-(3-(3-(4-octylphenyl)ureido)pyrrolidin-3-yl)acetate수율 80.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A solution of benzyl 3-(2-ethoxy-2-oxoethyl)-3-(3-(4-octylphenyl)ureido)pyrrolidine-1-carboxylate (140 mg, 0.26 mmol) in EtOH (5 mL) was purged with nitrogen and Pd/C (25 mg) was added and the flask was purged with hydrogen and stirred for 24 h. The mixture was filtered through celite and concentrated. The residue was dissolved into H2O and lyophilized to give the title compound as a white solid (84 mg, 80%). 1H NMR (400 MHz, CD3OD) δ 7.25 (d, 2H, J=7.9 Hz), 7.08 (d, 2H, J=8.1 Hz), 4.16 (q, 2H, J=7.1 Hz), 4.05-4.02 (m, 1H), 3.51-3.47 (m, 2H), 3.23-3.19 (m, 1H), 2.91-2.87 (m, 1H), 2.57-2.50 (m, 3H), 2.26-2.20 (m, 1H), 1.60-1.57 (m, 2H), 1.31-1.23 (m, 15H), 0.90 (t, 3H, J=6.6 Hz).

후처리

  1. additionwas added
  2. customthe flask was purged with hydrogen
  3. filtrationThe mixture was filtered through celite
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved into H2O

출처 및 근거

ORD 기록
ord-9762afc814284022be16a9bcee61835d
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680282B2

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