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

HRID 423038ノート

反応式

HRID 423038 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ddac0aa4e2424b8cbdcf299b8b53b0d5
出典データセット
uspto-grants-2012_01
特許番号
US08101623B2

反応ノート

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