ChemicalBook CAS DataBase List BOC-BETA-IODO-ALA-OME

BOC-BETA-IODO-ALA-OME synthesis

6synthesis methods

Product Name:BOC-BETA-IODO-ALA-OME
CAS Number:93267-04-0
Molecular formula:C9H16INO4
Molecular Weight:329.13

56926-94-4 Synthesis

56926-94-4
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$7.00/250mg

93267-04-0
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$5.00/250mg

Yield:93267-04-0 80%

Reaction Conditions:

with sodium iodide in acetone for 22 h;Inert atmosphere;

Steps:

2.2.1; 2.2.2; 2.2.3 Example 2.1 - Step 2: Lab Scale
The entire following procedure was performed in the dark. A 2-liter round bottom flask covered in foil was charged with the tosylate of BOC-L-serine methyl ester 2a (0.40 mol) and acetone (855 mL) under an atmosphere of nitrogen. While stirring, sodium iodide (1.0 mol) was added in one portion and allowed to stir for 22 h, at which time the reaction was complete by thin layer chromatography (30% ethyl acetate in heptane, KMnC stain, disappearance of 2a). The reaction mixture was added slowly over 1 h to 0-5 °C water (3 L) and stirred for 2 h at that temperature. The crude solids were filtered using a fritted funnel, washed with water (3x50 mL), then deliquored for 16 h. A 1-liter round bottom flask was charged with the crude solids and heptane (225 mL). The mixture was warmed to 35-40 °C at which point all of the solids had dissolved. A phase separation was performed and the lower aqueous layer was drained and discarded. The organic layer was cooled to -15 °C and stirred for 2 h. The solids were filtered using a fritted funnel and rinsed twice with the filtrate, then with clean, 0 °C, heptane (20 mL). The solids were dried in a vacuum drying oven at ambient temperature for 24 h, providing pure iodo- intermediate 3a in 80% yield.

References:

VISTAGEN THERAPEUTICS, INC.;LEVIN, Daniel;LEEMING, Peter;EISENREICH, Emerich;LIU, Xuejun, Karl WO2019/157426, 2019, A1 Location in patent:Paragraph 70-91

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2766-43-0 Synthesis