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

HRID 1637045노트

반응식

HRID 1637045 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-4de34b20a914461782e67151a4944bb6
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06037498

반응 노트

불러오는 중…