反应 #2006397

反应方程式

methyl chloroformate

(S)-2-amino-2-(tetrahydro-2H-pyran-4-yl)acetic acid

sodium carbonate

→

(S)-2-(methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acid

溶剂

water

反应条件

后处理

1. 1
   其他thaw to ambient temperature
2. 2
   其他The reaction mixture was then partitioned between 1N HCl and ethyl acetate
3. 3
   其他The organic layer was removed
4. 4
   萃取the aqueous layer was further extracted with 2 additional portions of ethyl acetate
5. 5
   洗涤The combined organic layers were washed with brine
6. 6
   干燥dried over magnesium sulfate
7. 7
   过滤filtered
8. 8
   浓缩concentrated in vacuo
9. 9
   其他to afford Cap-170 a colorless residue

实验过程

To (S)-2-amino-2-(tetrahydro-2H-pyran-4-yl)acetic acid (505 mg; 3.18 mmol; obtained from Astatech) in water (15 ml) was added sodium carbonate (673 mg; 6.35 mmol), and the resultant mixture was cooled to 0° C. and then methyl chloroformate (0.26 ml; 3.33 mmol) was added dropwise over 5 minutes. The reaction was allowed to stir for 18 hours while allowing the bath to thaw to ambient temperature. The reaction mixture was then partitioned between 1N HCl and ethyl acetate. The organic layer was removed and the aqueous layer was further extracted with 2 additional portions of ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to afford Cap-170 a colorless residue. 1H NMR (500 MHz, DMSO-d6) δ ppm 12.65 (1H, br s), 7.44 (1H, d, J=8.24 Hz), 3.77-3.95 (3H, m), 3.54 (3H, s), 3.11-3.26 (2H, m), 1.82-1.95 (1H, m), 1.41-1.55 (2H, m), 1.21-1.39 (2H, m); LC/MS: Anal. Calcd. for [M+H]+ C9H16NO5: 218.1. Found 218.1.

来源