Boron trifluoride etherate → (2S,3S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoate

HRID 523177ノート

反応式

HRID 523177 の反応式
[CH2:1]([C@H:3]1[N:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[C@@H:4]1[C:13]([O:15][CH3:16])=[O:14])[CH3:2].[CH3:17][C@@H:18]([OH:23])[CH2:19][CH2:20][CH:21]=[CH2:22].B(F)(F)F.O(CC)CC>C(Cl)Cl>[C:9]([O:8][C:6]([NH:5][C@@H:4]([C@@H:3]([O:23][C@@H:18]([CH2:19][CH2:20][CH:21]=[CH2:22])[CH3:17])[CH2:1][CH3:2])[C:13]([O:15][CH3:16])=[O:14])=[O:7])([CH3:12])([CH3:11])[CH3:10]

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 11848709(2R)-hex-5-en-2-olHCID 90118291(2S,3R)-1-tert-butyl 2-methyl 3-ethylaziridine-1,2-dicarboxylate

生成物 1

HCID 90118054(2S,3S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoate収率 43%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a round-bottom flask equipped with a stir bar was added (2S,3R)-1-tert-butyl 2-methyl 3-ethylaziridine-1,2-dicarboxylate (691, 3.02 mmol) and CH2Cl2 (12 mL). To the solution was added (R)-hex-5-en-2-ol (363 mg, 3.62 mmol), then BF3-OEt2 (1.0M in CH2Cl2, 0.30 mL). The solution was stirred at room temperature for 16 h. The solution was transfered to a separatory funnel and was diluted with CH2Cl2, then the solution was washed with aq. saturated NaHCO3; then brine. The organic phase was dried over Na2SO4; filtered; then concentrated in vacuo. The resulting residue was subjected to silica gel chromatography (hexanes:EtOAc 90:10 to 70:30) to afford (2S,3S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoate as a colorless oil (426 mg, 43%). 1H-NMR (500 MHz, CDCl3) δ 5.81 (ddt, J=17.0, 10.4, 6.5 Hz, 1H), 5.19 (d, J=7.7 Hz, 1H), 5.08-5.00 (m, 1H), 4.96 (dd, J=10.2, 1.7 Hz, 1H), 4.50 (dd, J=8.3, 3.5 Hz, 1H), 3.75 (s, 3H), 3.65-3.58 (m, 1H), 3.57-3.50 (m, 1H), 2.19-2.06 (m, 2H), 1.66-1.56 (m, 2H), 1.55-1.38 (m, 11H), 1.13 (d, J=6.1 Hz, 3H), 0.97 (t, J=7.3 Hz, 3H).

後処理

  1. customTo a round-bottom flask equipped with a stir bar
  2. customThe solution was transfered to a separatory funnel
  3. washthe solution was washed with aq. saturated NaHCO3
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthen concentrated in vacuo

出典と根拠

ORDレコード
ord-a1e30f0bc4904477b629e6498707bb29
出典データセット
uspto-grants-2016_05
特許番号
US09334279B2

反応ノート

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