Diethyl Ether → HCID 11187623、化合物

HRID 494865ノート

反応式

HRID 494865 の反応式
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[C:20]([C:24](=[O:26])[CH3:25])[CH:21]=[CH:22][CH:23]=3)=[CH:14][C:12]=2[CH:13]=1.[CH3:27][Mg]Br.CCOCC>O1CCCC1>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[C:20]([C:24]([OH:26])([CH3:27])[CH3:25])[CH:21]=[CH:22][CH:23]=3)=[CH:14][C:12]=2[CH:13]=1

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 9884652HCID 9884652、化合物HCID 178418573HCID 178418573、化合物

生成物 1

HCID 11187623HCID 11187623、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The product from Example 136C (87 mg, 0.25 mmol) was dissolved into tetrahydrofuran (5 mL), treated with 3 M methylmagnesium bromide in ether (0.3 mL, 0.9 mmol), stirred overnight, quenched with 0.5 M aqueous dipotassium hydrogen phosphate, and diluted with EtOAc and a little CH2Cl2. The resulting emulsion was sonicated, and the aqueous phase was separated and extracted with EtOAc. The combined organic phases were washed consecutively with 0.5 M aqueous dipotassium hydrogen phosphate and brine, dried (Na2SO4), concentrated, and chromatographed on silica with a gradient of 2 to 10% MeOH/20% MeCN/CH2Cl2 followed by 10% MeOH/CH2Cl2 to provide the title compound as an orange resin (˜33% yield). 1HNMR (300 MHz, CD3OD) δ 1.20 (d, 3H), 1.42-1.58 (m, 1H), 1.58 (s, 6H), 1.76-1.90 (m, 2H), 1.96-2.12 (m, 1H), 2.3-2.7 (m, 3H), 2.97-3.13 (m, 2H), 3.22-3.4 (m, 2H), 6.62 (s, 1H), 7.38 (dd, 1H), 7.40-7.46 (m, 2H), 7.46-7.48 (m, 2H), 7.72 (dd, 1H), 7.76 (dd, 1H).

後処理

  1. customquenched with 0.5 M aqueous dipotassium hydrogen phosphate
  2. additiondiluted with EtOAc
  3. customThe resulting emulsion was sonicated
  4. customthe aqueous phase was separated
  5. extractionextracted with EtOAc
  6. washThe combined organic phases were washed consecutively with 0.5 M aqueous dipotassium hydrogen phosphate and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customchromatographed on silica with a gradient of 2 to 10% MeOH/20% MeCN/CH2Cl2

出典と根拠

ORDレコード
ord-6f4ab93b83194ea1a9d510393ce34345
出典データセット
uspto-grants-2009_05
特許番号
US07538138B2

反応ノート

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