2,2-Diphenylacetyl chloride → HCID 86755897, compound

Participants

Reaction Steps

(R)-N5 -(Cbz)-(R)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide hydrochloride (28.1 g; 66.6 mmol; from step (c) above) was dissolved in THF (500 mL) and solid sodium bicarbonate (22.4 g; 266.4 mmol; 4 eq.) was slowly added. A solution of diphenylacetylchloride (21.4 g; 66.60 mmol) in THF was then slowly added dropwise over 30 minutes. The reaction was monitored by TLC analysis. After the reaction was judged complete, the solvent was removed under vacuum and the residue was dissolved in a mixture of THF, EtOAc and MeOH and washed with saturated aqueous sodium bicarbonate, water, saturated KHSO4 and brine. The organics were dried over Na2SO4, filtered and concentrated to dryness to yield 29.2 g (0.050 mol; 76%) of the sub-title compound.

Provenance & Evidence