Chlorine → HCID 68671999, compound

Participants

Reaction Steps

The arylated lactam (3S,5S)-di-tert-butyl-7-(3-chlorophenyl)-8-oxo-2,7-diazaspiro[4.4]nonane-2,3-dicarboxylate (A7a) (45.7 mg, 101 μmol) was taken up in 1M HCl in ethyl acetate (1.0 ml, 10 eq). The reaction was aged at room temperature overnight. The reaction was purged by bubbling N2 gas through it, until dry. The product was then taken up in a saturated solution of hydrochloric acid in methanol (2 ml), and aged at room temperature overnight. The reaction was blown dry with nitrogen gas and dried in-vacuo to give (3S,5R) methyl-7-(3-chlorophenyl)-8-oxo-2,7-diazaspiro[4.4]nonane-3-carboxylate (B7a) (35.2 mg, 102 μmol). LCMS for C15H17N2O3Cl 308.09 [M], found ES+ 309.2 [M+H]+ and 311.1 [M+H]+ (for the chlorine isotope) at 2.0 minutes retention time, using 5-45% acetonitrile/water (with 0.1% formic acid buffer) gradient over 7 minutes. The minor diastereomer (3S,5R)-di-tert-butyl 7-(3-chlorophenyl)-8-oxo-2,7-diazaspiro[4.4]nonane-2,3-dicarboxylate (A7b) (15.2 mg, 34 μmol) was treated similarly to give (3S,5S)-methyl 7-(3-chlorophenyl)-8-oxo-2,7-diazaspiro[4.4]nonane-3-carboxylate (B7b) (12.4 mg, 36 μmol). LCMS for C15H17N2O3Cl 308.09 [M], found ES+ 309.2 [M+H]+ and 311.1 [M+H]+ (for the chlorine isotope) at 2.2 minutes retention time, using 5-45% acetonitrile/water (with 0.1% formic acid buffer) gradient over 7 minutes.

Provenance & Evidence