FMOC-b-Ala-OH synthesis
- Product Name:FMOC-b-Ala-OH
- CAS Number:35737-10-1
- Molecular formula:C18H17NO4
- Molecular Weight:311.34
28920-43-6
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35737-10-1
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Yield:35737-10-1 81%
Reaction Conditions:
Stage #1:(fluorenylmethoxy)carbonyl chloride;3-amino propanoic acid with sodium carbonate in 1,4-dioxane;water at 0 - 20; for 4 h;
Stage #2: with hydrogenchloride in water; pH=2
Steps:
3
β-Alanine (β-Ala) (0.5 g, 6.61 mmole) was dissolved in 10% NaCO3 (12 ml) under stirring in a 50 ml flask. To the resulting solution, which had been put into an ice bath, Fmoc-Cl (1.45 g, 5.61 mmol) in dioxane (10 ml) was gradually added. The reaction mixture was stirred at room temperature for 4 hours, and water (80 ml) was then added. The aqueous phase layer was separated from the reaction mixture and stripped with ether three times (75 ml*3). The stripped aqueous layer was acidified with 2N HCl aqueous solution to a pH value of 2, followed by extraction with ethyl acetate three times (75 ml*3). The organic phase layer was recovered and concentrated to obtain crude product of 1.50 g. The crude product was recrystallized in a mixed solvent of ethyl acetate:hexane=1:2 (30 ml), and white solid denoted as Fmoc-β-Ala was obtained after filtration at a reduced pressure. Yield: 1.41 g (81%). NMR (CDCl3) δ 2.60 (t, 2H, NHCH2C2COOH), 3.47 (d, 2H, J=7.0 Hz, NHC2CH2COOH), 4.19 (t, 1H, J=6.0 Hz, Fmoc-C), 4.39 (d, 2H, J=7.0 Hz, Fmoc-C2), 7.29 (t, 2H, J=7.3 Hz, Ar-), 7.38 (t, 2H, J=7.3 Hz, Ar-), 7.56 (d, 2H, J=7.0 Hz, Ar-), 7.74 (d, 2H, J=7.5 Hz, Ar-).
References:
YUNG SHIN PHARM. IND. CO., LTD. US2009/131681, 2009, A1 Location in patent:Page/Page column 3
82911-69-1
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107-95-9
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35737-10-1
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82911-69-1
624 suppliers
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35737-10-1
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82911-69-1
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35737-10-1
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24324-17-2
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61-90-5
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82911-69-1
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35661-60-0
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35737-10-1
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24324-17-2
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