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ChemicalBook CAS DataBase List BOC-GLYCINE N,O-DIMETHYLHYDROXAMIDE
121505-93-9

BOC-GLYCINE N,O-DIMETHYLHYDROXAMIDE synthesis

9synthesis methods
13734-36-6 Synthesis
BOC-SAR-OH

13734-36-6
297 suppliers
$11.19/5G

6638-79-5 Synthesis
N,O-Dimethylhydroxylamine hydrochloride

6638-79-5
573 suppliers
$6.00/25g

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Yield: 95%

Reaction Conditions:

Stage #1:N-(tert-butoxycarbonyl)sarcosine with 1,1'-carbonyldiimidazole in tetrahydrofuran at 20; for 2 h;Inert atmosphere;
Stage #2:N,O-dimethylhydroxylamine*hydrochloride in tetrahydrofuran at 20;

Steps:

3.1d tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)(methyl)carbamate
To a solution of 2-((tert-butoxycarbonyl)(methyl)amino)acetic acid (25.0 g, 132.0 mmol) in 300 mL of anhydrous THF under N2 atmosphere was added CDI (1.2 eq; 25.7 g; 159.0 mmol) portionwise over 10 min. The reaction mixture was stirred at room temperature for 2 h and N,O-dimethylhydroxylamine hydrochloride (1.2 eq.; 15.5 g; 159 mmol) and Et3N (1.2 eq; 22.0 mL; 159.0 mmol) were added. The resolution was stirred overnight at room temperature. The precipitated salts were filtered off and the filtrate was concentrated. The residue was diluted with H2O (300 mL) and extracted with EtOAc (3×100 mL). Combined organic phases were washed with 10% KHSO4 (3×50 mL), saturated NaHCO3 (50 mL), water and brine, then dried over MgSO4 and concentrated. This gave tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)(methyl)carbamate as a colorless oil (29 g, 95%). 1H-NMR spectrum in DMSO-d6 indicates a mixture of rotamers (1:1). 1H NMR (DMSO-d6) δ: 4.08 (s, 1H), 4.07 (s, 1H), 3.68 (s, 1.5H), 3.66 (s, 1.5H), 3.10 (s, 1.5H), 3.09 (s, 1.5H), 2.82 (s, 1.5H), 2.78 (s, 1.5H), 1.39 (s, 4.5H), 1.33 (s, 4.5H). MS 132 (MH+).

References:

SENOMYX, INC.;Chumakova, Lyudmyla;Patron, Andrew;Priest, Chad;Karanewsky, Donald;Kimmich, Rachel;Boren, Brant Clayton;Hammaker, Jeffrey Robert;Chumakov, Volodymyr;Zhao, Wen;Noncovich, Alain;Ung, Jane US2015/376136, 2015, A1 Location in patent:Paragraph 0866

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