反应 #612798

反应方程式

hydrogen peroxide water

sodium bisulfate

Trifluoroacetic acid

product

benzyl (1-(5-(4-((1R,2S)-2-(2,2-difluoroacetamido)-3-fluoro-1-hydroxypropyl)phenyl)pyridin-2-yl)ethyl)carbamate

pyridine

THF

bis(benzyloxy)(diisopropylamino)phosphine

→

title product

benzyl (1-(5-(4-((1R,2S)-1-((bis(benzyloxy)-phosphoryl)oxy)-2-(2,2-difluoroacetamido)-3-fluoropropyl)phenyl)pyridin-2-yl)ethyl)carbamate

溶剂

water

反应条件

后处理

1. 1
   萃取The reaction mixture is extracted with ethylacetate (2×15 mL)
2. 2
   干燥The combined organics are dried over MgSO4
3. 3
   过滤filtered
4. 4
   其他evaporated
5. 5
   其他to give the crude product, which
6. 6
   其他is purified by silica chromatography
7. 7
   洗涤eluting from 25% ethylacetate/heptanes to neat ethylacetate

实验过程

Trifluoroacetic acid (51.6μL) is added to the product of step 3, Example 95A (0.168 g, 0.335 mmol) and pyridine (54.2μL, 0.67 mmol) in THF (4.4 mL, 54 mmol) at 0° C. After 5 minutes, bis(benzyloxy)(diisopropylamino)phosphine (0.219 mL, 0.586 mmol) is added. After allowing to warm to room temperature the mixture is stirred for 1 hour. 30% hydrogen peroxide/water (30:70, 60μL, 0.586 mmol) is added. After 1 hour sodium bisulfate (4 mL) is added and water (10 mL) is added. The reaction mixture is extracted with ethylacetate (2×15 mL). The combined organics are dried over MgSO4, filtered and evaporated to give the crude product, which is purified by silica chromatography eluting from 25% ethylacetate/heptanes to neat ethylacetate to give the title product (241 mg): m/z: 761.25.

来源