(S)-BOC-3-AMINO-2-PYRROLIDINONE

Step 1 : To a solution of 25b (3.1g, 32mmol) in methanol (13OmL) was added TEA (16mL) and (Boc)2O (7.7g, 35.2mmol) at room temperature. The mixture was stirred overnight at room temperature, followed by refluxing for 2h. Solvent was removed and the residue was purified by column chromatography (EA) to provide 40a (5.0g, 78percent) as white solid.Example 40 Preparation of 5-[5-Fluoro-2-oxo-1, 2-dihydro-indol-(3Z)-ylidenemethyl]-2, 4-dimethyl-1H-pyrrole-3-carboxylic acid ((S)-1-carbamoylmethyl-2-oxo-pyrrolidin-3-yl)-amide Preparation of 2-((S)-3-Amino-2-oxo-pyrrolidin-1-yl)-acetamide Step 1: To a solution of 25b (3.1 g, 32 mmol) in methanol (130 mL) was added TEA (16 mL) and (Boc)2O (7.7 g, 35.2 mmol) at room temperature. The mixture was stirred overnight at room temperature, followed by refluxing for 2 h. Solvent was removed and the residue was purified by column chromatography (EA) to provide 40a (5.0 g, 78percent) as white solid.General procedure for the synthesis of protected lactam intermediates (5) ; [00240] The general synthesis of protected lactam intermediates (5) is shown inScheme 2. Lactam (4) (6.5 mmol; prepared according to the general method of Example 1) is added to a solution of BOC anhydride (1.5 g, 6.9 mmol) and triethylamine (0.96 mL, 6.9 mmol) in dichloromethane (30 mL) in a round-bottom flask and the reaction is allowed to stir at ambient temperature for 16 hours. The reaction mixture is concentrated and precipitated with ether. The slurry is filtered, and the solids are dissolved in dichloromethane, filtered, and concentrated to yield the BOC-protected lactam (5). Example 6Preparation of (S)-tert-butv\ 2-oxopvrrolidin-3-vlcarbamate (5a) [00202] (S)-tert-Ruiy (2-Oxopyrrolidin-3-yl)carbamate (126) To a solution of 0.60 g (2.75 mmol) of BOC-L-DAB-OH in 275 mL of DMF at a 10 mM concentration were added 1.22 g (2.75 mmol) of BOP and 1.16 g (20.0 mmol) of sodium bicarbonate. After 12 h stirring at room temperature, the mixture was concentrated to a small volume (around 5 mL) under reduced pressure. The concentrated mixture was diluted with water and saturated sodium bicarbonate solution (1 : 1, 100 mL) and extracted with three 100- mL portions of EtOAc. The combined organic extracts were washed with 200 mL of water and 200 mL of brine, dried over NaStep 2:Tert-butyl N-[(3S)-2-oxopyrrolidin-3-yl] carbamate. To a solution of (35)-3- aminopyrrolidin-2-one (2.0 g, 20 mmol) and Et

Molecular Weight:200.23
XLogP3:0.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:200.11609238
Monoisotopic Mass:200.11609238
Topological Polar Surface Area:67.4
Heavy Atom Count:14
Complexity:245
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes