Dimethylformamide → Phenylmethyl N-(2-amino-2-oxoethyl)carbamate

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Reaction Steps

The amine trifluoroacetate from Example 4 (215 mg, 0.180 mmol) is dissolved in N,N-dimethylformamide (2 ml). To this solution 1M sodium bicarbonate (200 μl, 0.200 mmol) and pentafluorophenyl N-benzyloxycarbonylglycinate (106 mg, 0.270 mmol) is added. After 1 h, the reaction mixture is diluted with water (2×). Isolation by reverse-phase (C18) flash column chromatography eluting with acetonitrile/water gives, after lyophilization of the product-containing fractions, the N-CBZ glyamide: C61H92N10O19, formula weight=1269.47.

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