反応 #1808168

反応方程式

benzyl chloroformate

benzyl chloroformate

D-allylglycine

sodium hydroxide

sodium hydroxide

sodium hydroxide

→

title product

(R)-2-[[(Phenylmethoxy)carbonyl]amino]-4-pentenoic acid

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   温度then cooled in an ice-bath
2. 2
   workup.ADDITIONwere added
3. 3
   workup.STIRRINGThe reaction mixture was stirred for 15 minutes at 0° C.
4. 4
   抽出30 minutes at room temperature and then extracted with 50 mL of ether
5. 5
   workup.ADDITIONby addition of 6N hydrochloric acid solution (about 10 mL)
6. 6
   抽出then extracted with three-50 mL portions of ether
7. 7
   乾燥dried (magnesium sulfate)
8. 8
   濃縮concentrated in vacuo

実験手順

A mixture of D-allylglycine (2.8 g, 24.3 mmol), 1 M aqueous sodium hydroxide solution (25 ml), and tetrahydrofuran (10 ml, distilled from ketyl) was stirred at room temperature until homogeneous then cooled in an ice-bath. To the resulting rapidly stirred solution was added about 5 mL of 1.0M aqueous sodium hydroxide solution then dropwise about 1 g of benzyl chloroformate. This was repeated 4 additional times until a total of 28 mL of 1.0M aqueous sodium hydroxide solution and 4.80 g (95%, 27 mmol) of benzyl chloroformate were added. The reaction mixture was stirred for 15 minutes at 0° C. then 30 minutes at room temperature and then extracted with 50 mL of ether. The aqueous layer was acidified (pH=1.5) the by addition of 6N hydrochloric acid solution (about 10 mL) then extracted with three-50 mL portions of ether. The three ether extracts were combined, dried (magnesium sulfate) and concentrated in vacuo to afford 6.01 g of title product as a colorless oil.

出典