Dicyclohexylcarbodiimide → HCID 131716001, compound

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Reaction Steps

[1-[[N2 -(Cyclobutylcarbonyl)-N6 -[(phenylmethoxy) carbonyl]-L-lysyl]amino]-2-phenylethyl]phosphonic acid (500 mg., 0.91 mmole) is dissolved in pyridine (10 ml.) with 1-[(S)-6-[[(phenylmethoxy)carbonyl]amino]-2-hydroxy-1-oxohexyl]-L-proline, phenylmethyl ester (426 mg., 0.91 mmole). Dicyclohexylcarbodiimide (224 mg., 1.09 mmole) is added and the mixture is stirred at room temperature overnight. It is then concentrated in vacuo and partitioned between ethyl acetate and 5% potassium bisulfate after filtering to remove dicyclohexyl urea. The ethyl acetate layer is washed with brine, dried over sodium sulfate, and concentrated to give 1-[(S)-6-[[(phenylmethoxy)carbonyl]amino]-2-[[[1-[[(S)-6-[[(phenylmethoxy)carbonyl]amino]-2-[(cyclobutylcarbonyl)amino]-1-oxohexyl]amino]-2-phenylethyl]hydroxyphosphinyl]oxy]-1-oxohexyl]-L-proline, phenylmethyl ester as a crude oil. TLC (silica gel; dichloromethane:methanol:acetic acid, 20:1:1) Rf =0.33.

Provenance & Evidence