反应 #2122522

反应方程式

ClCO2Me

(R)-tert-butyl 2-amino-2-phenylacetate HCl

diisopropylethylamine

→

(R)-tert-butyl 2-(methoxycarbonylamino)-2-phenylacetate

收率 71.6%

溶剂

THF

反应条件

后处理

1. 1
   其他The volatile component was removed in vacuo
2. 2
   其他the residue was partitioned between water (100 mL) and ethyl acetate (200 mL)
3. 3
   洗涤The organic layer was washed with 1N HCl (25 mL) and saturated NaHCO3 solution (30 mL)
4. 4
   干燥dried (MgSO4)
5. 5
   过滤filtered
6. 6
   浓缩concentrated in vacuo
7. 7
   其他The resultant colorless oil was triturated from hexanes
8. 8
   过滤filtered
9. 9
   洗涤washed with hexanes (100 mL)

实验过程

ClCO2Me (3.2 mL, 41.4 mmol) was added dropwise to a cooled (ice/water) THF (410 mL) semi-solution of (R)-tert-butyl 2-amino-2-phenylacetate/HCl (9.877 g, 40.52 mmol) and diisopropylethylamine (14.2 mL, 81.52 mmol) over 6 min, and stirred at similar temperature for 5.5 hours. The volatile component was removed in vacuo, and the residue was partitioned between water (100 mL) and ethyl acetate (200 mL). The organic layer was washed with 1N HCl (25 mL) and saturated NaHCO3 solution (30 mL), dried (MgSO4), filtered, and concentrated in vacuo. The resultant colorless oil was triturated from hexanes, filtered and washed with hexanes (100 mL) to provide (R)-tert-butyl 2-(methoxycarbonylamino)-2-phenylacetate as a white solid (7.7 g). 1H NMR (DMSO-d6, δ=2.5 ppm, 400 MHz): 7.98 (d, J=8.0, 1H), 7.37-7.29 (m, 5H), 5.09 (d, J=8, 1H), 3.56 (s, 3H), 1.33 (s, 9H). LC (Cond. 1): RT=1.53 min; ˜90% homogeneity index; LC/MS: Anal. Calcd. for [M+Na]+ C14H16NNaO4: 288.12; found 288.15.

来源