HCID 59547338, compound → HCID 59547307, compound

Participants

Reaction Steps

The methyl ester (3S,5R)-methyl-7-(3-chlorophenyl)-2-((S)-2-(2-cyclohexylacetamido)-3,3-dimethyl butanoyl)-8-oxo-2,7-diazaspiro[4.4]nonane-3-carboxylate (E7a) (12.8 mg, 23 μmol) was taken up in THF (1.0 ml) and MeOH (50 μl) was added. To this was added 1N LiOH in water (46 μl, 2.0 eq). The reaction was stirred at room temperature overnight and quenched at 0° C. with 1N HCl in water (46 μl, 2.0 eq). The reaction was concentrated to dryness to give (3S,5R)-7-(3-chlorophenyl)-2-((S)-2-(2-cyclohexylacetamido)-3,3-dimethylbutanoyl)-8-oxo-2,7-diazaspiro[4.4]nonane-3-carboxylic acid (F7a) (23 μmol). LCMS for C28H38N3O5Cl 531.25 [M], found ES+ 532.3 [M+H]+ and ES− 530.5 [M−H]− at 3.2 minutes retention time, using 10-90% acetonitrile/water (with 0.1% formic acid buffer) gradient over 5 minutes. The minor diastereomer (3S,5S)-methyl 7-(3-chlorophenyl)-2-((S)-2-(2-cyclohexylacetamido)-3,3-dimethylbutanoyl)-8-oxo-2,7-diazaspiro[4.4]nonane-3-carboxylate (E7b) (6.6 mg, 12 μmol) was treated similarly to give (3S,5S)-7-(3-chlorophenyl)-2-((S)-2-(2-cyclohexylacetamido)-3,3-dimethylbutanoyl)-8-oxo-2,7-diazaspiro[4.4]nonane-3-carboxylic acid (F7b) (12 mmol). LCMS for C28H38N3O5Cl 531.25 [M], found ES+ 532.25 [M+H]+ and ES− 530.25 [M−H] at 3.3 minutes retention time, using 10-90% acetonitrile/water (with 0.1% formic acid buffer) gradient over 5 minutes.

Provenance & Evidence