反応 #1466509

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), 1M 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