Methyl iodide → Methyl (S)-3-((tert-butoxycarbonyl)amino)-3-(4-chlorophenyl)propanoate

HRID 423038노트

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HRID 423038 반응식
IC.[C:3]([O:7][C:8]([NH:10][C@H:11]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[CH2:12][C:13]([OH:15])=[O:14])=[O:9])([CH3:6])([CH3:5])[CH3:4].[C:23](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:3]([O:7][C:8]([NH:10][C@H:11]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[CH2:12][C:13]([O:15][CH3:23])=[O:14])=[O:9])([CH3:6])([CH3:4])[CH3:5]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 7010269(S)-3-((Tert-butoxycarbonyl)amino)-3-(4-chlorophenyl)propanoic acid

생성물 1

HCID 57750406Methyl (S)-3-((tert-butoxycarbonyl)amino)-3-(4-chlorophenyl)propanoate수율 128%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

Iodomethane (1.038 mL, 16.68 mmol) was added in one portion to (S)-3-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoic acid (1 g, 3.34 mmol) and potassium carbonate (0.922 g, 6.67 mmol) in DMF (15 mL). The resulting suspension was stirred at 80° C. for 24 hours. The reaction mixture was concentrated and diluted with EtOAc (50 mL) with water (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford (S)-methyl 3-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoate (1.340 g, 128%) as a orange solid. 1H NMR (399.9 MHz, DMSO-d6) δ 1.36 (9H, s), 2.71-2.74 (1H, m), 2.74-2.80 (1H, m), 3.57 (3H, s), 4.91 (1H, d), 7.33 (2H, d), 7.39 (2H, d), 7.49 (1H, d). m/z (ESI−) (M−H)−=312; HPLC tR=2.57 min.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with EtOAc (50 mL) with water (50 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-ddac0aa4e2424b8cbdcf299b8b53b0d5
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101623B2

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