Diethyl Ether → HCID 11187623, 화합물

HRID 1064757노트

반응식

HRID 1064757 반응식
[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

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 9884652HCID 9884652, 화합물HCID 178418573HCID 178418573, 화합물

생성물 1

HCID 11187623HCID 11187623, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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, 3 H), 1.42-1.58 (m, 1 H), 1.58 (s, 6 H), 1.76-1.90 (m, 2 H), 1.96-2.12 (m, 1 H), 2.3-2.7 (m, 3 H), 2.97-3.13 (m, 2 H), 3.22-3.4 (m, 2 H), 6.62 (s, 1 H), 7.38 (dd, 1 H), 7.40-7.46 (m, 2 H), 7.46-7.48 (m, 2 H), 7.72 (dd, 1 H), 7.76 (dd, 1 H).

후처리

  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

출처 및 근거

ORD 기록
ord-2d4246a3b30a4a56a96116b08ad8f410
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969730B2

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