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 1192902ノート

反応式

HRID 1192902 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9762afc814284022be16a9bcee61835d
出典データセット
uspto-grants-2014_03
特許番号
US08680282B2

反応ノート

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