반응 #64809

반응 방정식

N-methylmorpholine

isobutylchloroformate

N-[[(1,1-dimethylethyl)oxy]carbonyl]-L-phenylalanine

diazomethane

→

(S)-3-[[[(1,1-Dimethylethyl)oxy]carbonyl]amino]-2-oxo-1-diazo-4-phenylbutane

용매

methanol

tetrahydrofuran

ether

반응 조건

후처리

1. 1
   여과The reaction mixture was then filtered into a flask
2. 2
   온도let warm to -5° C.
3. 3
   workup.STIRRINGstirred overnight
4. 4
   기타The cold reaction mixture
5. 5
   여과was then filtered
6. 6
   세척the filtrate was washed with water, saturated sodium bicarbonate, and brine
7. 7
   건조The organic layer was dried (MgSO4)
8. 8
   여과filtered
9. 9
   농축concentrated in vacuo
10. 10
    기타to yield a reddish brown oil
11. 11
    기타The oil was triturated with cold petroleum ether
12. 12
    기타to yield 14.42 g
13. 13
    농축The mother liquors were concentrated
14. 14
    기타to stand yielding a second crop of 1.96 g

실험 절차

A solution of N-[[(1,1-dimethylethyl)oxy]carbonyl]-L-phenylalanine (20.01 g., 75 mmol) in 150 mL of dry tetrahydrofuran was chilled to -25° C. and treated with N-methylmorpholine (8.3 mL, 75 mmol) and isobutylchloroformate (9.8 mL, 75 mmol) and then stirred at -25° C. for 10 minutes. The reaction mixture was then filtered into a flask containing a solution of diazomethane (prepared from 35.48 g., 240 mmol of N-methyl-N'-nitro-N-nitroso-guanidine) in 300 mL of anhydrous ether at -78° C. and then let warm to -5° C. and stirred overnight. The cold reaction mixture was then filtered and the filtrate was washed with water, saturated sodium bicarbonate, and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to yield a reddish brown oil. The oil was triturated with cold petroleum ether to yield 14.42 g. of a light tan solid. The mother liquors were concentrated and allowed to stand yielding a second crop of 1.96 g. of light yellow crystals for a total yield of 16.38 g. of the title A compound as a tannish solid; m.p. 87°-90° C. [α]D =-32.2° (c=1.15, methanol).

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