ChemicalBook CAS DataBase List BOC-GLYCINE N,O-DIMETHYLHYDROXAMIDE

BOC-GLYCINE N,O-DIMETHYLHYDROXAMIDE synthesis

9synthesis methods

Product Name:BOC-GLYCINE N,O-DIMETHYLHYDROXAMIDE
CAS Number:121505-93-9
Molecular formula:C9H18N2O4
Molecular Weight:218.25

13734-36-6 Synthesis

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

6638-79-5 Synthesis

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

121505-93-9
130 suppliers
$6.00/1g

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 N₂atmosphere 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 MgSO₄and 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-d₆indicates 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

4530-20-5 Synthesis