ChemicalBook CAS DataBase List Moc-Leu-OH

Moc-Leu-OH synthesis

4synthesis methods

Product Name:Moc-Leu-OH
CAS Number:74761-37-8
Molecular formula:C8H15NO4
Molecular Weight:189.21

61-90-5 Synthesis

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Yield:74761-37-8 100%

Reaction Conditions:

Stage #1: L-leucine;methyl chloroformatewith sodium hydroxide in 1,4-dioxane;lithium hydroxide monohydrate at 0 - 60; pH=8 - 9; for 18 h;
Stage #2: with hydrogenchloride in lithium hydroxide monohydrate;

Steps:

11.1

Step 1: Synthesis of ( S )-2 -( methoxycarbonylamino)-4-methylpentonoic acid:A stirred solution of (S)-2-amino-4-methylpentanoic acid (about 5.0 g, 38. 16 mmol) in Dioxane (20 ml) at 0 °C 2N NaOH (62 ml, P^H = 8-9) and methychloioformate (5.88 ml, 76.33 mmol) were added drop wise and stirred at about 60 °C for about 18 hours. The reaction mixture was cooled to room temperature, extracted with DCM, the aqueous layer was separated and acidified with I N HCl. The resulting solution was extracted with EtOAc, dried over Na₂S0₄ and the solvent was evaporated under the reduced pressure and the resulting crude was stirred in he.xane and decanted to afford the title compound as a semi solid. Wt: 8.0 g: Yield: quantitative; NMR (300 MHz, CDC1₃): δ 5.09 (d, 1 H, J = 8.4 Hz), 4.43-4.3 1 (m, 1 H), 3.7 1 (s, 3H), 1 .80- 1 .39 (m, 3H), 0.96 (d, 6H, J = 6. 1 Hz); Mass: [M+H]⁺ 190 (60%) [M+Na]⁺ 2.12 ( 100%); IR (KBr, cm^{" 1} ): 3354, 2960, 1709, 1540, 1467, 1456, 1370, 1270, 1235, 1 123, 1058, 924, 781 .

References:

WO2011/80562,2011,A1 Location in patent:Page/Page column 42