(S)-methyl 3-((S)-1-phenylethylamino)butanoate → HCID 11830202、化合物

HRID 1637046ノート

反応式

HRID 1637046 の反応式
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

参加物

4

反応物 2

HCID 11096167(S)-methyl 3-((S)-1-phenylethylamino)butanoateHCID 178418573HCID 178418573、化合物

生成物 1

HCID 11830202HCID 11830202、化合物

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-dbc7dc97ba914fc794e8005c19f34ca0
出典データセット
uspto-grants-2000_03
特許番号
US06037498

反応ノート

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