反応 #302881

反応方程式

TFA

(2S)-2 Benzyloxycarbonylamino-5-oxo-heptanedioic acid 1-benzyl ester 7-ethyl ester

resorcinol

ether

→

L-(7-hydroxycoumarin-4-yl) ethylglycine

収率 50.0%

溶媒

methanesulfonic acid

water

CH3CN

反応条件

後処理

1. 1
   温度was cooled to −30° C
2. 2
   洗浄The precipitate was washed with cold ether
3. 3
   workup.DISSOLUTIONdissolved in water
4. 4
   ろ過filtered
5. 5
   その他L-(7-hydroxycoumarin-4-yl)ethylglycine was purified by reverse phase HPLC
6. 6
   その他to afford a brown solid in 50% yield (YMC AA12S052503WT column, 12 ml/min flow rate
7. 7
   その他over the course of 12 min

実験手順

(2S)-2 Benzyloxycarbonylamino-5-oxo-heptanedioic acid 1-benzyl ester 7-ethyl ester from the previous step (2.35 g, 5 mmol) was added slowly to resorcinol (3 g, 25 mmol) in methanesulfonic acid (20 ml) and stirred for two hours at room temperature. Five volumes of ether were then added to the mixture and was cooled to −30° C. The precipitate was washed with cold ether, dissolved in water, filtered, and lyophilized. L-(7-hydroxycoumarin-4-yl)ethylglycine was purified by reverse phase HPLC to afford a brown solid in 50% yield (YMC AA12S052503WT column, 12 ml/min flow rate, from 10% to 90% CH3CN, 0.1% TFA (w/v) in water, over the course of 12 min). 1H-NMR (DMSO): δ 2.06 (s, 2H), 2.70-2.90 (m, 2H), 3.82-4.0 (m, 1H), 6.06 (s, 1H), 6.75 (dd, J=8.8, 2.4, 1H), 6.82 (d, J=2.4, 1H), 7.62 (d, J=8.8, 1H), 8.17 (s, 3H). LC-MS (ESI) calc. for C13H14NO5 (M+H+) 264.08 Da, obsd. 264.0 Da.

出典