反応 #64855

反応方程式

BOC-L-Ala

serinol hydrochloride

N-methylmorpholine

HOBT

H2O

1,3-dicyclohexylcarbodiimide

→

crude product

BOC-L-Ala-SerOH

溶媒

acetic acid

DMF

CH2Cl2

DMF

反応条件

後処理

1. 1
   workup.ADDITIONtreated dropwise with a solution that
2. 2
   workup.STIRRINGThe reaction mixture was stirred at RT for 20 hours
3. 3
   workup.STIRRINGstirred for another hour
4. 4
   その他The solid reaction by-products
5. 5
   その他were removed by filtration
6. 6
   洗浄washed with 20 ml CH2Cl2
7. 7
   濃縮The combined filtrate and washings was concentrated to dryness on the rotary evaporator
8. 8
   その他then further dried under high vacuum
9. 9
   温度cooled at 4° C. for several hours
10. 10
    ろ過filtered
11. 11
    濃縮The filtrate was concentrated to dryness on the rotary evaporator
12. 12
    その他further dried under high vacuum

実験手順

BOC-L-Ala (567 mg, 2 mMol) and HOBT.H2O (505 mg, 3.3 mMol) were dissolved in 5 ml CH2Cl2 and 5 ml DMF, then treated with 1,3-dicyclohexylcarbodiimide (DCC, 680 mg, 3.3 mMol). The resulting solution was stirred at RT for one hour, then treated dropwise with a solution that contained 421 mg (3.3 mMol) of serinol hydrochloride (Aldrich) and 333 mg (3.3 mMol) of N-methylmorpholine in 5 ml of DMF. The reaction mixture was stirred at RT for 20 hours, then treated with 0.5 ml of glacial acetic acid and stirred for another hour. The solid reaction by-products were removed by filtration and washed with 20 ml CH2Cl2. The combined filtrate and washings was concentrated to dryness on the rotary evaporator then further dried under high vacuum. The oily residue was taken up in 50 ml of H2O, cooled at 4° C. for several hours, then filtered. The filtrate was concentrated to dryness on the rotary evaporator, then further dried under high vacuum to yield the crude product as a yellow oil.

出典