ChemicalBook CAS DataBase List (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate synthesis

12synthesis methods

Product Name:(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate
CAS Number:220587-29-1
Molecular formula:C21H32BNO6
Molecular Weight:405.29

73183-34-3
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266306-18-7 Synthesis

N-Boc-4-broMo-L-phenylalanine Methyl ester

266306-18-7
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(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

220587-29-1
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Yield: 100%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium acetate in 1,4-dioxane at 90;Inert atmosphere;Sealed tube;

Steps:

Scheme 2, Step 2: Preparation of methyl (S)-2-(tert- butoxycarbonyl)amino)-3-(4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)propanoate (33)
To a round bottom pressure vessel was added methyl (,S)-3-(4-bromophenyl)-2-((tert- butoxycarbonyl)amino)propanoate (compound 32, 2 g, 5.58 mmol), bis(pinacolato) diboron (1.84 g, 7.26 mmol), Pd(dppf)Cl2 (0.245 g, 0.335 mmol), potassium acetate (1.64 g, 16.7 mmol) and 1,4-dioxane (20 mL). The vessel was sparged with nitrogen gas for 10 minutes, sealed, and heated overnight at 90 °C. The reaction was filtered through a plug of Celite and rinsed with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, then filtered and concentrated in vacuo. The resulting oil was purified on silica gel using ethyl acetate and hexanes as eluent. Product methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)propanoate (2.26 g, quant, yield) was isolated as an oil. LC-MS: t_R=2.70 min; m/z+23=428.2.

References:

SAINT LOUIS UNIVERSITY;WASHINGTON UNIVERSITY;RUMINSKI, Peter, G.;MEYERS, Marvin, L.;HEIER, Richard, F.;RETTIG, Michael, P.;DIPERSIO, John WO2018/85552, 2018, A1 Location in patent:Page/Page column 70-71