反応 #75427

反応方程式

sodium hydroxide

hydrochloric acid

methyl chloroformate

D-phenylalanine

sodium hydroxide

→

oil

収率 113.9%

(R)-2-(Methoxycarbonylamino)-3-phenylpropanoic acid

収率 113.9%

溶媒

water

tetrahydrofuran

water

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONWhen the addition
2. 2
   workup.ADDITIONwas also added dropwise
3. 3
   抽出The acid was extracted twice with diethylether
4. 4
   洗浄the extracts were washed with brine
5. 5
   乾燥dried (MgSO4)
6. 6
   その他The solvent was removed under vacuum

実験手順

A solution of D-phenylalanine (25.00 g, 0.151 mol) and sodium hydroxide (6.05 g, 0.151 mol) in water (170 ml) and tetrahydrofuran (225 ml) was cooled to −15° C., and a solution of methyl chloroformate (18.6 g, 0.197 mol) in tetrahydrofuran (50 ml) was added dropwise. When the addition was ˜half complete, a solution of sodium hydroxide (9.10 g, 0.227 mol) in water (20 ml) was also added dropwise. When the additions were complete, the mixture was stirred at room temperature for an additional 2 hours and acid fixed with 10% hydrochloric acid. The acid was extracted twice with diethylether, and the extracts were washed with brine and dried (MgSO4). The solvent was removed under vacuum to leave a clear oil (38.38 g). HPLC 6.01 min (78.9%), 7.32 min (5.0%), 8.29 min (10.8%), 8.42 min (0.5%), 9.95 min (1.2%), 10.27 min (2.8%), 11.92 min (0.7%).

出典