Methyl Acrylate → 3-[Benzyloxycarbonyl-((R)-2-tert-butoxycarbonylamino-1-methyl-ethyl)-amino]-propionic acid methyl ester

Participants

Reaction Steps

72 g (413 mmol) ((R)-2-amino-propyl)-carbamic acid tert-butyl ester were dissolved in MeOH (350 ml) in a jacketed reactor. A solution of 40 ml (438 mmol) methyl acrylate in MeOH (50 ml) was added over 10 min. After 15 h reaction at RT, 108 g (413 mmol) of N-benzyloxycarbonyloxy-succinimide were added in one portion. After 18 h, the reaction mixture was concentrated under reduced pressure affording a yellow oil (ca 270 g). The oil was re-dissolved in 300 mL MeOH and concentrated under reduced pressure (45° C./160-200 mbar) until constant weight to give 219 g of crude titled product as a yellow oil used directly in the next step.

Provenance & Evidence