Hydrochloric Acid → (S)-methyl 3-((S)-1-phenylethylamino)butanoate

HRID 1637045ノート

反応式

HRID 1637045 の反応式
[CH3:1][C@H:2]([NH:9][C@@H:10]([CH3:19])[CH2:11][C:12]([O:14][C:15](C)(C)C)=[O:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>CO>[CH3:15][O:14][C:12](=[O:13])[CH2:11][C@@H:10]([NH:9][C@@H:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH3:19]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 11139971(3S,alphaS)-t-Butyl 3-(alpha-methylbenzylamino)butanoate

生成物 1

HCID 11096167(S)-methyl 3-((S)-1-phenylethylamino)butanoate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of compound (29) from Example 14 (1.00 mmol) was stirred in a saturated solution of gaseous hydrogen chloride in methanol for 30 minutes. The solvent was then removed under reduced pressure. This procedure was repeated until no starting material remained. The white solid residue was diluted with ethyl acetate (30 ml), washed with saturated aqueous sodium bicarbonate (2×30 ml), water (20 ml) and brine (20 ml), dried (magnesium sulphate) and filtered, and the solvent was evaporated under reduced pressure to give the title compound (35) as a clear oil. [α]D21 -45.5 (c 1.95, CHCl3); νmax (CHCl3)/cm-1 1736 s (C=O); δH (300 MHz; CDCl3) 7.34-7.20 (5H, m, Ph), 3.88 (1H, q, J=6.5, PhCHCH3), 3.67 (3H, s, OCH3), 2.99 (1H, m, CH3CHCH2), 2.47, 2.38 (2H, ABX system, JAB =14.8, JAX =5.4, JBX =6.5, CH2CO), 1.33 (3H, d, J=6.5 PhCHCH3), 1.06 (3H, d, J=6.4, CH3CHCH2); δC (50 MHz; CDCl3) 173.01 (C=O), 146.29 (Ph:Cipso), 128.63, 126.70 (Ph:Cortho, Cmeta), 127.07 (Ph:Cpara), 55.15, 47.69 (CHN), 51.30 (OCH3), 40.52 (CH2CO), 24.54, 21.34 (NCHCH3); m/z (CI) 222 (MH+, 100%), 206 (15), 148 (10), 118 (5), 105 (10); (Found: C, 70.48; H, 8.80. C13H19NO2 requires C, 70.56; H, 8.65%).

後処理

  1. customThe solvent was then removed under reduced pressure
  2. additionThe white solid residue was diluted with ethyl acetate (30 ml)
  3. washwashed with saturated aqueous sodium bicarbonate (2×30 ml), water (20 ml) and brine (20 ml)
  4. dry with materialdried (magnesium sulphate)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-4de34b20a914461782e67151a4944bb6
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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