4-Ethylphenyl isocyanate → (1-(2-(Tert-butoxycarbonylamino)acetyl)-4-(3-fluoro-2-methylbenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate

HRID 655971ノート

反応式

HRID 655971 の反応式
[F:1][C:2]1[C:3]([CH3:31])=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][NH:6][C:7]([C:9]1([CH2:26][OH:27])[CH2:14][CH2:13][N:12]([C:15](=[O:25])[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:11][CH2:10]1)=[O:8].[CH2:32]([C:34]1[CH:39]=[CH:38][C:37]([N:40]=[C:41]=[O:42])=[CH:36][CH:35]=1)[CH3:33]>C1COCC1.CN(C1C=CN=CC=1)C>[CH2:32]([C:34]1[CH:39]=[CH:38][C:37]([NH:40][C:41](=[O:42])[O:27][CH2:26][C:9]2([C:7](=[O:8])[NH:6][CH2:5][C:4]3[CH:28]=[CH:29][CH:30]=[C:2]([F:1])[C:3]=3[CH3:31])[CH2:14][CH2:13][N:12]([C:15](=[O:25])[CH2:16][NH:17][C:18]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:24])[CH2:11][CH2:10]2)=[CH:36][CH:35]=1)[CH3:33]

参加物

5

反応物 2

HCID 900074-Ethylphenyl isocyanateHCID 59778520Tert-butyl 2-(4-(3-fluoro-2-methylbenzylcarbamoyl)-4-(hydroxymethyl)piperidin-1-yl)-2-oxoethylcarbamate

生成物 1

HCID 59778453(1-(2-(Tert-butoxycarbonylamino)acetyl)-4-(3-fluoro-2-methylbenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate収率 5%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of crude tert-butyl 2-(4-(3-fluoro-2-methylbenzylcarbamoyl)-4-(hydroxymethyl)piperidin-1-yl)-2-oxoethylcarbamate (185 mg, ˜0.422 mmol, 1.0 equiv.) in THF (2 mL) were added DMAP (10 mg, 0.085 mmol, 0.2 equiv.) and 4-ethylphenylisocyanate (61 μL, 0.422 mmol, 1.0 equiv.). The reaction mixture was stirred overnight, and then concentrated. The resulting residue was purified on RP-HPLC using a mixture of acetonitrile and H2O to give (1-(2-(tert-butoxycarbonylamino)acetyl)-4-(3-fluoro-2-methylbenzylcarbamoyl)piperidin-4-yl)methyl 4-ethylphenylcarbamate (12 mg, 5% for three steps). LRMS (M-Boc+H+) m/z 485.2.

後処理

  1. concentrationconcentrated
  2. customThe resulting residue was purified on RP-HPLC
  3. additiona mixture of acetonitrile and H2O

出典と根拠

ORDレコード
ord-b88831fd15a6409fb4e1f6029c86bb34
出典データセット
uspto-grants-2011_12
特許番号
US08071625B2

反応ノート

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