(2-Methoxyethoxy)acetic acid → HCID 69536205, compound

Participants

Reaction Steps

A mixture of (R)-3-amino-3-[4-(tert-butoxycarbonylamino)phenyl]-propanoic acid methyl ester [0.75 g, Reference Example 7(c)], 2-(2-methoxyethoxy)acetic acid (0.3 ml), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1.02 g), diisopropylethylamine (0.9 ml) and dimethylformamide (25 ml) was stirred at ambient temperature 2 hours. The reaction mixture was poured into water (150 ml) and the resultant solid collected. The resulting fawn solid (1.5 g) was dissolved in dichloromethane (15 ml) and the solution was treated with trifluoracetic acid (3 ml). After stirring at ambient temperature for 2 hours the reaction mixture was evaporated. The residue was treated with toluene (50 ml), concentrated to dryness and the resultant material treated with ethyl acetate (50 ml). The resultant suspension was treated with saturated aqueous potassium carbonate solution (20 ml) with stirring at ambient temperature for 5 minutes. The organic layer was separated, dried over magnesium sulphate, and then evaporated to give the title compound (0.5 g) as a yellow oil.

Provenance & Evidence