1-(tert-Butoxycarbonyl)-3-phenylproline → HCID 23560060, compound

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1-(tert-Butoxylcarbonyl)-3-phenylprolyl-N-(2-{[(tert-butoxycarbonyl)amino]methyl}-5-chlorobenzyl)-L-prolinamide was prepared as a mixture of diastereomers from 1-(tert-Butoxycarbonyl)-3-phenyl-D,L-proline (88 mg, 0.30 mmol) from the previous step and L-prolin-N-(2-{[(tert-butoxycarbonyl)amino]methyl}-5-chlorobenzyl)amide (111 mg, 0.30 mmol) essentially according to the EDC coupling procedure described in Step 3 of Example 46. The diastereomeric products separated under the following analytical conditions: Chiralcel OD (250×4.6 m) column eluting with A/B 85/15 where A=hexane/0. 1% diethylamine and B=ethanol, with detection at 220 nm and flow rate of 1.0 mL/min. Under these conditions, the early peak elutes at 4.87 min. and later peak at 8.51 min. The products were separated on preparative scale using these conditions. Diastereomer A: LCMS RT=2.72 min. LCMS (M+H)=641.2. Diastereomer B: LCMS RT=2.75 min. LCMS (M+H)=641.0

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