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

Reaction equation

C(=O)(O)[O-].[Na+].[CH2:6]([O:13][C:14]([NH:16][CH2:17][C:18]([O:20]C1C(F)=C(F)C(F)=C(F)C=1F)=O)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C[N:33](C)C=O>O>[NH:16]([C:14]([O:13][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:15])[CH2:17][C:18]([NH2:33])=[O:20]

Participants

Procedure

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.