Glycine methyl ester hydrochloride → Methyl (2-((tert-butoxycarbonyl)amino)ethyl)glycinate

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Reaction Steps

Boc-aminoacetaldehyde (19, 1.00 g, 6.3 mmol, 1 eqv) was dissolved in methanol (50 ml). Anhydrous sodium acetate (1.03 g, 12.6 mmol, 2 eqv), glycine methyl ester hydrochloride (Aldrich Chemical Co., 0.79 g, 6.3 mmol, 1 eqv) and sodium cyanoborohydride (1.97 g, 31.4 mmol, 5 eqv) were added to the solution in that order. The reaction mixture was stirred for 2 h at room temperature under nitrogen. Water (50 ml) was added to the suspension and the resulting clear solution was evaporated under reduced pressure to remove the methanol. The aqueous phase was extracted with methylene chloride (3×100 ml). The organic phase was washed with a saturated aqueous solution of sodium chloride (1×100 ml), dried (Na2SO4), filtered and then evaporated under reduced pressure affording 1.41 g of crude title compound as a yellow oil. The crude product was kugelrohr distilled at 110° C. and 0.5 mbar to yield 0.49 g (34%) of 2-(Boc-amino)ethylglycine methyl ester as a colorless liquid. 1H-NMR (CDCl3 /TMS): δ=1.36 (s, 9H, Me3C), 1.91 (s, 1H, NH), 2.67 (t, J=6 Hz, 2H, NHCH2), 3.13 (q, J=6 Hz, 2H, NHCH2), 3.34 (s, 2H, CH2CO0), 3.65 (s, 3H, OMe), 5.13 (b, 1H, carbamate NH). 13C-NMR (CDCl3 /TMS): δ=28.2 (Me3C), 39.9, 48.5 (NHCH2), 50.0 (CH2COO), 51.5 (OMe), 78.9 (Me3C), 155.9 (carbamate C=O), 172.6 (ester C=O). Anal. Calcd for C10H2N2O4 : C, 51.71; H, 8.68; N, 12.06. Found: C, 51.55; H, 8.72; N, 11.79.

Provenance & Evidence