Triethylamine → HCID 68818218、化合物

HRID 736756ノート

反応式

HRID 736756 の反応式
[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([NH:23][CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH:25]3[C:30]([OH:32])=[O:31])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[C:40]([N:44]=[C:45]=[O:46])([CH3:43])([CH3:42])[CH3:41]>C1COCC1>[C:40]([NH:44][C:45]([N:27]1[CH2:28][CH2:29][C@@H:24]([NH:23][S:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=[C:2]([CH3:1])[CH:11]=3)=[CH:15][CH:16]=2)(=[O:21])=[O:22])[C@@H:25]([C:30]([OH:32])=[O:31])[CH2:26]1)=[O:46])([CH3:43])([CH3:42])[CH3:41]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 68817351HCID 68817351、化合物

生成物 1

HCID 68818218HCID 68818218、化合物収率 88.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

To a solution of 0.5 g (1.1 mmol) of 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-3-carboxylic acid (Example 29, Step 1) and triethylamine (0.3 mL, 2.197 mmol) in THF (10 mL) at 0° C. was added tert-butylisocyanate (0.130 g, 1.32 mmol). The reaction mixture was allowed to warm to 25° C. and then stirred for 19 h. The THF was removed in vacuo and the resulting oil was diluted with ethyl acetate (100 mL). The organics were washed with saturated aqueous sodium chloride (2×30 mL), dried over MgSO4, filtered and concentrated to obtain a crude solid (0.580 g). The crude product was purified by reverse phase HPLC (Gilson) on a Phenomex C-18 semi-prep column eluting an acetonitrile:water gradient, to afford (3S,4R)-1-tert-butylcarbamoyl-4-[4-(2-methyl-quinolin-4-yl methoxy)-benzenesulfonylamino]-piperidine-3-carboxylic acid as an amorphous white solid (0.5 g, 88.5%). MS: 555 (M+H)+.

後処理

  1. customThe THF was removed in vacuo
  2. additionthe resulting oil was diluted with ethyl acetate (100 mL)
  3. washThe organics were washed with saturated aqueous sodium chloride (2×30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto obtain a crude solid (0.580 g)
  8. customThe crude product was purified by reverse phase HPLC (Gilson) on a Phenomex C-18 semi-prep column
  9. washeluting an acetonitrile

出典と根拠

ORDレコード
ord-7fa93891e7794a458c31375477419356
出典データセット
uspto-grants-2009_09
特許番号
US07595327B2

反応ノート

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