(S)-methyl 3-((S)-1-phenylethylamino)butanoate → HCID 11830202, 화합물

HRID 1637046노트

반응식

HRID 1637046 반응식
C[O:2][C:3](=O)[CH2:4][C@@H:5]([NH:7][C@@H:8]([CH3:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:6].C[Mg]Br>C(OCC)C>[CH3:15][C@H:8]([N:7]1[C@@H:5]([CH3:6])[CH2:4][C:3]1=[O:2])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

4

반응물 2

HCID 11096167(S)-methyl 3-((S)-1-phenylethylamino)butanoateHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 11830202HCID 11830202, 화합물

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution compound (35) from Example 21 (1.00 mmol) in anhydrous diethyl ether (5 ml) at 0° C. was added slowly, dropwise, 3.0 M methylmagnesium bromide (1.10 mmol). The resulting solution was stirred for 10 minutes and the reaction was then quenched by addition of pH7 buffer. Diethyl ether (20 ml) was added, whereafter the solution was washed with water (20 ml) and brine (20 ml), dried (magnesium sulphate) and filtered. The solvent was removed under reduced pressure to afford the title compound (41) as a clear oil which was subjected to flash chromatography on silica gel. [α]D21 -68.9 (c 1.61, CHCl3); νmax (CHCl3)/cm-1 1742 s (C=O), δH (300 MHz; CDCl3) 7.34-7.23(5H, m, Ph), 4.92 (1H, q, J=7.2, PhCHCH3), 3.51 (1H, m, CH3CHCH2); 2.97, 2.46 (2H, ABX system, JAB =14.4, JAX =5.1, JBX =2.4, CH2CO), 1.63 (3H, d, J=7.2, PhCHCH3), 1.25 (3H, d, J=6.1, CH3CHCH2); δC (50 MHz; CDCl3) 166.90 (C=O), 140.67 (Ph:Cipso), 128.85, 127,18 (Ph:Cortho,Cmeta), 127.77 (Ph: Cpara), 51.78, 47.18 (CHN), 43.45(CH2CO), 20.65, 19.25 (NCHCH3); m/z (CI) 190 (MH+, 100%), 174(5), 132 (10), 105 (8); (Found: C, 76.02; H, 7.98; 7.07. C12H15NO requires C, 76.16; H, 7.99; N, 7.40%).

후처리

  1. customthe reaction was then quenched by addition of pH7 buffer
  2. additionDiethyl ether (20 ml) was added, whereafter the solution
  3. washwas washed with water (20 ml) and brine (20 ml)
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-dbc7dc97ba914fc794e8005c19f34ca0
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06037498

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