Water → HCID 118194618, compound

Participants

Reaction Steps

A diastereomeric mixture of (S)-ethyl 2,2-diethoxy-3-(((S)-1-phenylethyl)amino)hexanoate (6.4 g, d.r.: 85:15) was dissolved in 100 mL iPr2O and 2 mL water were added. The mixture was acidified to pH=2.21 with 50% H2SO4 and the resulting organic phase was concentrated to half its volume (50 mL). 1 mL water was added, and the mixture was acidified again to pH=2.22 with 50% H2SO4. The aqueous phase was combined with the aqueous phase from the previous extraction (V=1.5 mL) and extracted with 11 mL DIPET (diisopropyl ether) after adjusting the pH to 2.17 with 5M NaOH. The combined organic phases were concentrated (V=40 mL), 1 mL water was added and the mixture was acidified to pH=2.18 with 50% H2SO4. The organic phase was separated and the solvent was removed in vacuo to yield a 98:2 (syn:anti) mixture of diastereomers (37.5 mL solution, assay: 28%, 76% yield).

Provenance & Evidence