ChemicalBook CAS DataBase List Z-Lys(Z)-OH

Z-Lys(Z)-OH synthesis

11synthesis methods

Product Name:Z-Lys(Z)-OH
CAS Number:405-39-0
Molecular formula:C22H26N2O6
Molecular Weight:414.45

A 250 mL three-necked flask was loaded consecutively with water (20 mL), 1,4-dioxane (20 mL), and L-lysine (2.1 g, 14.4 mmol). The mixture was stirred until complete dissolution. The pH was adjusted to about 10.5 by the addition of 30% NaOH. Benzyl chloroformate (5.2 g, 30.6 mmol) was added while maintaining the pH at about 1011 by adding at the same time 30% NaOH. At the end of the addition, the reaction was stirred at 20° C. for about 1 hour. The pH was adjusted to 5 with 37% HCl. Ethyl acetate (30 mL) was added and the pH was adjusted to 1 with 37% HCl. The mixture was stirred at room temperature for about 30 minutes, the organic layer was separated and the aqueous layer was extracted with ethyl acetate (20 mL). The combined organic layer was washed with brine (30 mL) and dried over Na2SO4. Then, the solvent was evaporated to yield Z-Lys(Z)-OH as a yellowish oil (6.0 g, 99%).

1155-64-2 Synthesis

1155-64-2
301 suppliers
$6.00/5g

501-53-1
393 suppliers
$10.00/1g

405-39-0
184 suppliers
$11.00/5g

Yield: 99%

Reaction Conditions:

with sodium carbonate in 1,4-dioxane;water; pH=Ca. 10 - 11 at 20; for 1 h;

Steps:

34 Preparation of Compound 24e
Preparation of Compound 24e A three-necked flask was loaded consecutively with H₂O (40 mL), 1,4-dioxane (70 mL) and H-Lys(Z)-OH (10 g, 35.7 mmol). The mixture was stirred until complete dissolution. The pH was adjusted to about 10.5 by adding of 2 M aqueous Na₂CO₃. Benzyl chloroformate (6.69 g, 39.2 mmol) was added while maintaining the pH at about 10-11 by adding at the same time 2 M aqueous Na₂CO₃. After completing addition, the reaction mixture was stirred at 20 °C for 1 hour. Then EtOAc (50 mL) was added and pH of the resulting mixture was adjusted to 2-3 with c-HCl. The organic layer was separated and the aqueous layer was extracted with EtOAc (50 mL). The combined organic layers were washed with brine (50 mL), and dried over Na₂SO₄. Filtration and concentration under reduced pressure yielded the compound 24e as yellowish oil (14.7g, 99 %). ¹H-NMR (400 MHz, CDC1₃) δ 7.33-7.27 (m, 10H), 5.07-5.04 (d, 4H), 4.08 (m, 1H), 3.09 (t, 2H), 1.51 (br s, 1H), 1.49 (bs, 1H), 1.47-1.40 (m, 4H).

References:

LEGOCHEM BIOSCIENCES, INC.;KIM, Yong, Zu;OH, Yeong, Soo;CHAE, Jeiwook;SONG, Ho, Young;CHUNG, Chul-woong;PARK, Yun, Hee;CHOI, Hyo, Jung;PARK, Kyung, Eun;KIM, Hyoungrae;KIM, Jinyeong;MIN, Ji, Young;KIM, Sung, Min;LEE, Byung, Soo;WOO, Dong, Hyun;JUN, Ji, Eun;LEE, Su, In WO2017/89890, 2017, A1 Location in patent:Page/Page column 117

56-87-1 Synthesis

56-87-1
716 suppliers
$5.00/5g

501-53-1
393 suppliers
$10.00/1g

405-39-0
184 suppliers
$11.00/5g

References

L-Lysine, N6-[(phenylmethoxy)carbonyl]-, methyl ester

24498-31-5
1 suppliers
inquiry

501-53-1
393 suppliers
$10.00/1g

405-39-0
184 suppliers
$11.00/5g

References

L-Lysine, N2,N6-bis[(phenylmethoxy)carbonyl]-, 1,1-dimethylethyl ester

144889-39-4
0 suppliers
inquiry

405-39-0
184 suppliers
$11.00/5g

References

4-HYDROXYPHENYLDIMETHYLSULFONIUM METHYL SULFATE

32279-04-2
31 suppliers
$70.00/5g

405-39-0
184 suppliers
$11.00/5g

References

Z-Lys(Z)-OH Related Search:

Z-LYS(Z)-ONP Z-LYS(Z)-SER-OH N-alpha-Cbz-L-lysine Z-LEU-OH DCHA Z-LYS(BOC)-OH DCHA Z-LYS(BOC)-OH Z-LYS(BOC)-OSU Z-LYS(BOC)-ONP Fmoc-Lys(Boc)-OH FMOC-LYS(BIOTIN)-OH