Acetic Acid → 2-{[(Benzyloxy)carbonyl]amino}-2-(2,3-dihydro-1-benzofuran-5-yl)acetic acid

Participants

Reaction Steps

N-Benzyloxycarbonyl-α-hydroxyglycine (10.4 g., 0.046 mole) was added to a stirred mixture of concentrated sulfuric acid (4 ml.) and glacial acetic acid (36 ml.) at 0°-5° C. followed, after five minutes, by the dropwise addition of 2,3-dihydrobenzo(b)furan (5.8 g., 0.048 mole). The reaction mixture was stirred at ambient temperature overnight and the resulting pale mauve emulsion poured into stirred ice and water to afford a gum, which was induced to solidify. The crude product was collected, washed with water, dried in vacuo, and crystallized from a mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.) to provide Dl-α-benzyloxycarbonylamino-2,3-dihydro-5-benzo(b)furanyl acetic acid (5.3 g.), m.p. 121°-123° C. Recrystallization of a sample raised the m.p. to 125°-126° C.

Provenance & Evidence