4-Methylmorpholine → N-Hydroxy-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamide

HRID 727522Notes

Reaction equation

Cl.CN(C)CCCN=C=NCC.[CH3:13][CH:14]([CH3:34])[CH2:15][C:16]1([CH2:30][C:31](O)=[O:32])[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]1=[O:29].O.[OH:36][N:37]1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.NO>C(Cl)Cl.CN(C=O)C>[OH:36][NH:37][C:31](=[O:32])[CH2:30][C:16]1([CH2:15][CH:14]([CH3:34])[CH3:13])[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]1=[O:29]

Participants

Conditions

Temperature: 0 °C

Procedure

Solid 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 451 mg, 2.35 mmol) is added to a solution of 3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetic acid (595 mg, 1.96 mmol), 1-hydroxybenzotriazole hydrate (HOBT, 281 mg, 2.08 mmol) and 4-methylmorpholine (0.26 mL, 2.4 mmol) in CH2Cl2 (19 mL) and DMF (4 mL) at 0° C. The solution is stirred at 0° C. for 1 hour, and then a near solution of hydroxylamine hydrochloride (204 mg, 2.94 mmol) and 4-methylmorpholine (0.32 mL, 2.9 mmol) in DMF (2.7 mL) is added. After stirring at room temperature overnight, the mixture is concentrated under high vacuum, and purified by column chromatography (3% MeOH/CH2Cl2). Crystallization from Et2O/hexane provided 193 mg (31%) of the title compound as a white solid (mp 123°-124° C.).

Workup

stirringAfter stirring at room temperature overnight
concentrationthe mixture is concentrated under high vacuum
custompurified by column chromatography (3% MeOH/CH2Cl2)
customCrystallization from Et2O/hexane

Sources & evidence

ORD record: ord-7bf46e31e2f7413d8e593444a0b5c494
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712300

Reaction notes

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