Phenacyl bromide → 2-Oxo-2-phenylethyl (2R)-2-Propyloctanoate

HRID 1727337

반응식

HRID 1727337 반응식
[CH2:1]([C@H:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:5]([OH:7])=[O:6])[CH2:2][CH3:3].C(N(CC)CC)C.Br[CH2:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24].CC#N.O>C(Cl)Cl>[CH2:1]([C@H:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:5]([O:7][CH2:22][C:23](=[O:24])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:6])[CH2:2][CH3:3]

참가 물질

6

반응물 4

HCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 208925(R)-(-)-2-propyloctanoic acidHCID 18373917Acetonitrile--water (1/1)

생성물 1

HCID 117164482-Oxo-2-phenylethyl (2R)-2-Propyloctanoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(R)-2-propyloctanoic acid (0.05 g, 0.268 mmol) was dissolved in 5 mL, CH2Cl2. Triethylamine (50 μL, 0.359 mmol) and 2-bromoacetophenone (0.06 g, 0.300) were added, and the reaction was stirred at room temperature for 5 hours. Once no SM was seen by TLC, the reaction mixture was concentrated under reduced pressure to remove all triethylamine. The residue was purified by silica-gel chromatography (0-10% EtOAc:hexanes) to give the product (Example 2). Ee of >98.5% was determined by HPLC [Chiralcel OJ-RH 4.6×150 mm; CH3CN/H2O=60/40; flow rate 1 mL min−1; detection, 244 nm; retention time, 10.7 min (S) and 11.9 min (R).] 1H-NMR (CDCl3, 500 MHz) δ 7.91 (d, 2H), 7.61-7.57 (m, 1H), 7.48 (t, 2H), 5.32 (s, 2H), 2.55-2.50 (m, 1H), 1.72-1.68 (m, 2H), 1.52-1.48 (m, 2H), 1.47-1.27 (m, 10H), 0.93 (t, 3H), 0.88 (t, 3H).

후처리

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto remove all triethylamine
  3. customThe residue was purified by silica-gel chromatography (0-10% EtOAc:hexanes)
  4. customto give the product (Example 2)

출처 및 근거

ORD 기록
ord-1b1277b0a8894eff8e725331c3034a10
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495029B2

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