反応 #502129

反応方程式

Example 45b

2-((tert-Butoxy)-N-methylcarbonylamino)ethyl(2S)-2-(6-methoxy(2 naphthyl))propanoate

TFA

→

product

2-(Methylamino)ethyl(2S)-2-(6-methoxy(2-naphthyl))propanoate

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他The ice bath was removed
2. 2
   その他was evaporated
3. 3
   workup.ADDITIONThe residue was treated with aqueous sodium carbonate (10%)
4. 4
   抽出extracted with EtOAc
5. 5
   洗浄The combined organic extracts were washed with water, brine
6. 6
   乾燥dried over sodium sulfate
7. 7
   その他the solvent was evaporated

実験手順

The product of the Example 45b (17.1 g, 50 mmol) was dissolved in CH2Cl2 (400 mL). The solution was cooled to 0° C. and TFA (80 mL) was added drop-wise. The ice bath was removed and the reaction mixture was stirred at room temperature overnight, then the solvent. was evaporated. The residue was treated with aqueous sodium carbonate (10%) and extracted with EtOAc. The combined organic extracts were washed with water, brine, dried over sodium sulfate, and the solvent was evaporated. Trituration of the resulting solid with hexane gave the pure product as a white solid. Mp 64-68° C. 1HNMR (300 MHz, CDCl3) δ 7.67 (d, J=8.5 Hz, 2H), 7.66 (d, J=1.3, 1H), 7.4 (dd, J=8.5 and 1.8 Hz, 1H), 7.18-7.08 (m, 2H), 4.18 (t, J=5.4 Hz, 2H), 3.89 (s, 3H), 3.80 (q, J=7.1 Hz, 1H), 2.73 (t, J=5.4 Hz, 2H), 2.31 (s, 3H), 1.56 (d,l J=7.1 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 174.5, 157.6, 135.6, 133.6, 129.2, 128.8, 127.1, 126.1, 125.8, 118.9, 105.5, 63.9, 55.2, 50.0, 45.3, 36.0, 18.4.

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