反应 #67656

反应方程式

sodium triacetoxyborohydride

product

N-[(2R)-2-(thiazol-5-ylmethoxycarbonylamino)-3-phenylpropyl]-N-[(2S)-2-(thiazol-5-ylmethoxycarbonylamino)-3-phenylpropyl]amine

trimethylacetaldehyde

NaHCO3

acetic acid

→

title compound

收率 13.0%

N-(2,2-dimethylpropyl)-N-[(2R)-2-(thiazol-5-ylmethoxycarbonylamino)-3-phenylpropyl]-N-[(2S)-2-(thiazol-5-ylmethoxycarbonylamino)-3-phenylpropyl]amine

收率 13.0%

溶剂

1,2-dichloroethane

反应条件

后处理

1. 1
   workup.STIRRINGAfter stirring at ambient temperature for 24 hours
2. 2
   萃取extract with ethyl acetate (3×10 mL)
3. 3
   洗涤wash with brine (20 mL)
4. 4
   干燥dried over sodium sulfate
5. 5
   过滤filtered
6. 6
   浓缩the filtrate was concentrated
7. 7
   其他The residue was purified on a silica gel cartridge
8. 8
   洗涤eluting with chloroform

实验过程

The product from Example 26D (87.5 mg, 0.155 mmol) in 1,2-dichloroethane (3.0 mL) was treated with trimethylacetaldehyde (21 μL, 0.186 mmol) at ambient temperature. After stirring for 15 minutes, the mixture was treated with acetic acid (11 μL, 0.181 mmol) followed by sodium triacetoxyborohydride (53 mg, 0.248 mmol). After stirring at ambient temperature for 24 hours, the mixture was treated with aqueous 10% NaHCO3 (5.0 mL) and extract with ethyl acetate (3×10 mL). The ethyl acetate extracts were combined, wash with brine (20 mL), dried over sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified on a silica gel cartridge eluting with chloroform to provide the title compound (12.5 mg, 13%). 1H NMR (CDCl3) δ 8.73 (s, 2H), 7.79 (s, 2H), 7.28-7.05 (m, 10H), 5.20 (s, 4H), 4.88-4.76 (br s, 2H), 3.90-3.66 (m, 2H), 2.87 (dd, 2H), 2.75-2.60 (m, 2H), 2.47 (d, 4H), 2.17 (s, 2H), 0.78 (s, 9H); MS (ESI+) m/z 636 (M+H)+.

来源