FMOC-b-Ala-OH synthesis
- Product Name:FMOC-b-Ala-OH
- CAS Number:35737-10-1
- Molecular formula:C18H17NO4
- Molecular Weight:311.34
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35737-10-1
Under stirring conditions, β-alanine (β-Ala, 0.5 g, 6.61 mmol) was dissolved in 10% aqueous Na2CO3 solution (12 ml) in a 50 ml flask. The flask was cooled in an ice bath followed by slow dropwise addition of Fmoc-Cl (1.45 g, 5.61 mmol) in dioxane (10 ml) solution. The reaction mixture was stirred continuously for 4 hours at room temperature. After completion of the reaction, the aqueous phase layer was separated by adding water (80 ml) for dilution and washed three times (75 ml each) with ether. The aqueous phase layer was acidified to pH=2 with 2N HCl aqueous solution and subsequently extracted with ethyl acetate three times (75 ml each). The organic phase layers were combined and concentrated to give 1.50 g of crude product. The crude product was recrystallized by a solvent mixture of ethyl acetate and hexane (1:2, 30 ml, v/v) and filtered under reduced pressure to obtain a white solid, Fmoc-β-Ala. yield: 1.41 g (81%). NMR (CDCl3) δ 2.6 (t, 2H, NHCH2CH2COOH), 3.47 (d, 2H, J = 7.0 Hz, NHCH2CH2COOH), 4.19 (t, 1H, J = 6.0 Hz, Fmoc-CH), 4.39 (d, 2H, J = 7.0 Hz, Fmoc-CH2), 7.29 (t, 2H , J = 7.3 Hz, Ar-H), 7.38 (t, 2H, J = 7.3 Hz, Ar-H), 7.56 (d, 2H, J = 7.0 Hz, Ar-H), 7.74 (d, 2H, J = 7.5 Hz, Ar-H).
28920-43-6
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107-95-9
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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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35737-10-1
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24324-17-2
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