Methyl iodide → (S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-cyanopropanoate

HRID 1171962노트

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HRID 1171962 반응식
IC.[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH2:15][C:16]#[N:17])[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:18]1CCN2C(=NCCC2)CC1.OS([O-])(=O)=O.[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:18][O:13][C:12](=[O:14])[C@@H:11]([NH:10][C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[CH2:15][C:16]#[N:17]

참가 물질

8

반응물 4

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516920Potassium bisulfateHCID 7019873Boc-beta-cyano-L-alanine

생성물 1

HCID 76850178(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-cyanopropanoate수율 86.3%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

Iodomethane (2.18 ml, 35.01 mmol) was added to a mixture of (S)-2-(tert-butoxycarbonylamino)-3-cyanopropanoic acid (5.00 g, 23.34 mmol) and DBU (3.67 ml, 24.51 mmol) in toluene (20 mL) at rt. The reaction was stirred at 50 C for 2 days. Water (20 mL), saturated KHSO4 (20 mL) and ethyl acetate (50 mL) were added. The organic layer was separated, washed with brine and dried over sodium sulfate. After removal of solvent, the residue was purified by chromatography (hexane:Ethyl acetate=2:1) to give the (S)-methyl-2-(tert-butoxycarbonylamino)-3-cyanopropanoate as white solid (4.6 g, 86%). 1H NMR (400 MHz, d6-DMSO) δ7.64 (d, J=8.8 Hz, 1H), 4.39 (m, 1H), 3.66 (s, 3H), 2.96 (dd, J=16.8 Hz & 5.1 Hz, 1H), 2.85 (dd, J=16.8 Hz & 5.2 Hz, 1H), 1.40 (s, 9H).

후처리

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of solvent
  5. customthe residue was purified by chromatography (hexane:Ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-a49283446fa94e4398bd2209b4db3a85
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829665B2

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