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