Triethylamine → HCID 86592945、化合物

HRID 1245398ノート

反応式

HRID 1245398 の反応式
[CH3:1][O:2][C:3](=[O:30])[CH:4]=[CH:5][CH:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[C:21]([CH3:29])[CH:20]=3)=[CH:13][CH:12]=2)[CH2:7]1.[C:31]([OH:34])(=[S:33])[CH3:32].C(N(CC)CC)C>>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH:5]([S:33][C:31](=[O:34])[CH3:32])[CH:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[C:21]([CH3:29])[CH:20]=3)=[CH:13][CH:12]=2)[CH2:7]1

参加物

4

反応物 3

HCID 8471TriethylamineHCID 69640073HCID 69640073、化合物HCID 178418634HCID 178418634、化合物

生成物 1

HCID 86592945HCID 86592945、化合物収率 63%

実験手順

A suspension of the product from step 11a (1.0 g, 2.5 mmol), thioacetic acid (3.0 mL), and triethylamine (0.25 mL, 1.8 mmol) was stirred for 6 h at room temperature while slowly becoming a clear solution. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with aqueous sodium bicarbonate (2×), brine, dried over magnesium sulfate, and concentrated to give the crude product. This was purified by FCC on silica gel eluting ethyl acetate:hexanes (gradient) to give 3-acetylsulfanyl-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl ester (0.74 g, 63%) as an oil. MS found: (M+H)+=479.

後処理

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with aqueous sodium bicarbonate (2×), brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give the crude product
  6. customThis was purified by FCC on silica gel
  7. washeluting ethyl acetate

出典と根拠

ORDレコード
ord-d1e9e5bb369e4743a6a550c16ce11e28
出典データセット
uspto-grants-2006_10
特許番号
US07125870B2

反応ノート

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