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To a stirred suspension of (R^-Boc-morpholine-S-carboxylic acid (3Og, 0.13 moles, from J&W PharmLab) in 500 ml of anhydrous DCM at room temperature under nitrogen, N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (37.4g, 0.195 moles) and 1-hydroxybenzotriazole hydrate (19.3g, 0.143 moles) were added in portions. At the end of addition the suspension became almost a clear solution. The mixture was stirred at room temperature for 45 minutes and then Methyl Lambda/-(phenylmethyl)-D-serinate (D102, 28.6g, 0.137 moles) and N1N- diisopropylethylamine (45.3 ml, 0.26 moles) were added in small portions. The EPO <DP n="98"/>mixture was stirred at room temperature for 26 hours and then was additioned with ammonium chloride (sat. solution, 250 ml) and DCM (150 ml). Phases were separated and the aqueous layer was extracted with DCM (3 x 150 ml) and EtAc (1 x 200ml). The combined organic extracts were washed with brine (2 x 500 ml), dried (Na2SO4), concentrated under vacuum and the residue purified by silica gel chromatography eluting with 0 to 30% EtOAc/Cyclohexane to afford the title compound as yellow oil (38.7g). UPLC/MS: peak at Rt = 0.62 min with m/z = 423.1 [M+H]+
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