Sodium cyanoborohydride → HCID 70197038, compound

Participants

Reaction Steps

A mixture of N-(2-{[(3R,4R)-1-benzyl-4-{(3-methylbutyl)[(4-nitrophenyl)sulfonyl]amino}pyrrolidin-3-yl]amino}ethyl)-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide (see Example 1, Step 12) (200 mg, 0.259 mmol) was dissolved in 20:1 MeCN—AcOH (3.5 mL) and 37% aqueous formaldehyde was added (0.68 mL) following by addition of NaBH3CN (49 mg, 0.78 mmol). The mixture was stirred at ambient temperature for 3 hours and quenched with water (50 mL). The mixture was extracted with CHCl3, the combined organic extracts were dried with Na2SO4 and evaporated. The residue was passed through silica gel layer eluting with 1% MeOH in CHCl3. The solvent was evaporated giving the desired compound. LC-MS APCI: m/z 785.3 [M+H]+.

Provenance & Evidence