ChemicalBook CAS DataBase List Z-VAL-LEU-OH

Z-VAL-LEU-OH synthesis

7synthesis methods

Product Name:Z-VAL-LEU-OH
CAS Number:17708-79-1
Molecular formula:C19H28N2O5
Molecular Weight:364.44

4817-93-0
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17708-79-1
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Yield:17708-79-1 65%

Reaction Conditions:

with water monomer;lithium hydroxide monohydrate in tetrahydrofuran at 0 - 20;

Steps:

1 [0373] (S)-2-((S)-2-(((Benzyloxy)carbonyl)amino)-3-methylbutanamido)-4- methylpentanoic acid (4a)

[0374] The peptide 11a (500 mg, 1.14 mmol) was dissolved in THF/H₂O (1:1, 10 mL).LiOH (114 mg, 2.86 mmol) was added at 0 °C. The mixture was stirred at room temperature overnight. Then THF was removed on vacuum and the aqueous layer was acidified with 1 M HCl and extracted with dichloromethane (3 x 10 mL). The organic layer was dried over anhydrous Na₂SO₄ and concentrated to yield 4a as white solid (315 mg, 65%). ¹H NMR (CDCl₃, 400 MHz): δ 7.26- 7.23 (m, 5H), 6.65 (d, J=7.88, 1H), 5.68 (d, J=4.64 Hz, 1H), 5.03 (s, 2H), 4.56-4.45 (m, 1H), 3.97 (t, J=7.92 Hz, 1H), 2.02-1.96 (m, 1H), 1.66-1.46 (m, 3H), 0.85 (dd, J= 7.36, 13.3 Hz, 12H); ¹³C NMR (CDCl₃, 100 MHz): δ 176.0, 171.8, 156.7, 136.1, 128.5 (2C), 128.2, 128.0 (2C), 67.2, 60., 50.8, 41.1, 31.1, 24.8, 22.8, 21.8, 19.1, 18.0.

References:

WO2022/20711,2022,A1 Location in patent:Paragraph 0370; 0373-0374

7517-19-3 Synthesis