Sodium hydride → HCID 67130938, compound

HRID 1890436Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.[H-].[Na+].[C:16]([O:20][C:21]([N:23]1[CH2:26][CH:25]([CH2:27]OS(C)(=O)=O)[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C>[C:16]([O:20][C:21]([N:23]1[CH2:26][CH:25]([CH2:27][N:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[CH:7]=[CH:8][C:9]2=[O:13])[CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 7-methoxy-2(1H)-quinolinone (405 mg; commercial) in DMF (10 mL) was treated with NaH (111 mg; 50% dispersion in oil). The mixture was stirred at rt for 30 min before the addition of a solution of 3-[[(methylsulfonyl)oxy]methyl]-1-azetidinecarboxylic acid tert-butyl ester (674 mg; prepared according to WO 02/066470) in DMF (2 mL). The mixture was heated at 100° C. overnight. The reaction mixture was partitioned between EA and water. The org. phase was dried over MgSO4, concentrated under reduced pressure and purified by CC (Hept/EA 2:1 to 0:1). The second eluting compound was isolated as a colourless foam (350 mg, 44% yield).

Workup

customThe reaction mixture was partitioned between EA and water
dry with materialphase was dried over MgSO4
concentrationconcentrated under reduced pressure
custompurified by CC (Hept/EA 2:1 to 0:1)

Sources & evidence

ORD record: ord-c769a287126248d1b7a108a116885929
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507478B2

Reaction notes

Loading…