Formaldehyde → t-butyl hydroxymethylacrylate

Participants

Reaction Steps

 In a typical procedure, t-butyl acrylate (III) is reacted with paraformaldehyde in the presence of 3-quinuclidinol to provide t-butyl hydroxymethylacrylate (IV). This is first treated with thionyl chloride in the presence of triethylamine and pyridine to provide the corresponding chloromethylacrylate, which is then reacted with (S,S)-α-α′-dimethyldibenzylamine to provide an acrylate of the formula (V). This is converted to a compound of the formula (IX) by the method set out in Tet. Lett., 1993, 34(8), 1323-6. A compound of the formula (IX) is then condensed with a lysine derivative of the formula (X) by a similar procedure to that described in EP-A-0358398 for the preparation of a compound of the formula (XI). A compound of the formula (XI) is then converted to a compound of the formula (II) using a solution of trifluoroacetic acid and anisole in dichloromethane.

Provenance & Evidence