反応 #1539620

反応方程式

EDCI HCl

3-(3-iodo-4-hydroxyphenyl)-2-propenoic acid

tyrosine ethyl ester

NMP

NMP

→

3-(3-iodo-4-hydroxyphenyl)-2-propenoic acid tyrosine ethyl ester

溶媒

ethyl acetate

反応条件

後処理

1. 1
   その他To a 250 mL 3-necked round bottomed flask equipped with an overhead stirrer
2. 2
   その他is obtained
3. 3
   温度The flask may be cooled in an ice-water bath
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   その他The cooling bath may be removed after 2.5 hours
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   その他the reaction
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   workup.STIRRINGstirring may
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   温度be maintained for 15 more minutes
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   その他The crude may then be transferred into a 500 mL separatory funnel
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   抽出extracted once with 75 mL of brine
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    乾燥The organic phase may be dried over magnesium sulfate
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    workup.ADDITIONtreated with activated carbon
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    ろ過filtered
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    濃縮concentrated to a thick syrup, which
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    その他may crystallize into a solid mass after a few hours
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    その他The product may be triturated in methylene chloride using mechanical stirring
16. 16
    ろ過it may be recovered by filtration
17. 17
    その他dried under a nitrogen stream

実験手順

To a 250 mL 3-necked round bottomed flask equipped with an overhead stirrer may be added 17.0 g of 3-(3-iodo-4-hydroxyphenyl)-2-propenoic acid, 12.25 g (0.0585 moles) or tyrosine ethyl ester, and 25 mL of NMP. The mixture may be stirred until a clear solution is obtained. The flask may be cooled in an ice-water bath, the 11.84 g (0.0619 moles) of EDCI HCl may be added in one portion, followed by 15 mL of NMP. The cooling bath may be removed after 2.5 hours, and the reaction may be allowed to continue overnight at room temperature. 71 mL of ethyl acetate may be added, and stirring may be maintained for 15 more minutes. The crude may then be transferred into a 500 mL separatory funnel, and extracted once with 75 mL of brine, then with two aliquots (75 and 35 mL) of 3% NaHCO3/14% NaCl, followed by 35 mL aliquots of 0.4M HCl/14% NaCl, and finally with brine. The organic phase may be dried over magnesium sulfate and treated with activated carbon, filtered and concentrated to a thick syrup, which may crystallize into a solid mass after a few hours. The product may be triturated in methylene chloride using mechanical stirring, then it may be recovered by filtration and dried under a nitrogen stream followed by high vacuum.

出典