Sulfur → HCID 88214287、化合物

HRID 2269307ノート

反応式

HRID 2269307 の反応式
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C@@H:15]([C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[C:25]2[S:29][C:28](=[O:30])[NH:27][C:26]2=[O:31])=[CH:20][CH:19]=1)[O:16][CH3:17].[S]>C1COCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][CH:15]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C@@H:25]2[S:29][C:28](=[O:30])[NH:27][C:26]2=[O:31])=[CH:20][CH:19]=1)[O:16][CH3:17]

参加物

4

反応物 2

HCID 5362487SulfurHCID 88215764HCID 88215764、化合物

生成物 1

HCID 88214287HCID 88214287、化合物収率 35%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The title compound of Example 17 (640 mg, 1.5 mmol) was dissolved in THF (50 mL) and hydrogenated in the presence of sulfur-resistant 10% palladium on carbon (640 mg) on a Parr Shaker at 50 PSI for 20 hours. The catalyst was removed via filtration through diatomaceous earth and the filtrate was concentrated in vacuo. The residue was purified on silica gel, eluting with hexane/ethyl acetate (3/1) plus 5% acetic acid, to afford crude material which was further purified by (dissolving the residue in 50 mL of ethyl acetate, washing with water (25 mL), saturated aqueous sodium bicarbonate (25 mL), brine (25 mL) and drying (MgSO4), to afford a colorless gum (229 mg, 35%). 1HNMR (300 MHz, CDCl3): δ2.0 (m, 2H), 2.3 (s, 3H), 2.5 (t, 2H), 3.1 (dd, 1H), 3.2 (s, 3H), 3.5 (dd, 1H), 4.1 (dd, 1H), 4.4 (dd, 1H), 7.2 (m, 4H), 7.4 (m, 3H), 7.9 (m, 2H), 8.1 (bs, 1H, NH).

後処理

  1. customThe catalyst was removed via filtration through diatomaceous earth
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified on silica gel
  4. washeluting with hexane/ethyl acetate (3/1) plus 5% acetic acid
  5. customto afford crude material which
  6. customwas further purified by (
  7. dissolutiondissolving the residue in 50 mL of ethyl acetate
  8. washwashing with water (25 mL), saturated aqueous sodium bicarbonate (25 mL), brine (25 mL)
  9. dry with materialdrying (MgSO4)

出典と根拠

ORDレコード
ord-4b3b75f3c0404fc49bec5eeccbd7c3e1
出典データセット
uspto-grants-2001_12
特許番号
US06329408B1

反応ノート

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