Cesium carbonate → 7-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3-methyl-1,2-benzoxazole-5-carboxylic acid

HRID 577960Notes

Reaction equation

[Cl:1][C:2]1[C:3]([N:17]2[CH2:22][C@H:21]([CH3:23])[O:20][C@H:19]([CH3:24])[CH2:18]2)=[C:4]([CH:9]=[C:10]([C:13](=[N:15][OH:16])[CH3:14])[C:11]=1F)[C:5]([O:7]C)=[O:6].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[C:11]2[O:16][N:15]=[C:13]([CH3:14])[C:10]=2[CH:9]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[N:17]1[CH2:22][C@H:21]([CH3:23])[O:20][C@H:19]([CH3:24])[CH2:18]1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of methyl 3-chloro-2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-4-fluoro-5-[N-hydroxyethanimidoyl]benzoate (Intermediate 171, 700 mg, 1.94 mmol) in DMF (4 mL) was added Cs2CO3 (1.9 g, 5.84 mmol) and the mixture was heated to 130° C. for 14 hours. The reaction mixture was cooled to room temperature and filtered through a celite bed. The solvent was removed under vacuum and the residue was purified by silica gel chromatography column using ethyl acetate-pet. ether gradient to obtain product. Yield: 250 mg, (41%).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through a celite bed
customThe solvent was removed under vacuum
customthe residue was purified by silica gel chromatography column
customto obtain product

Sources & evidence

ORD record: ord-885d43109bd34a2b9bb3e2f758bb002e
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040528B2

Reaction notes

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