Ethyl Bromide → HCID 86639861, compound

HRID 1920095Notes

Reaction equation

[OH-].[K+].[F:3][C:4]1[CH:5]=[C:6]([N:20]2[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]2=[O:30])[CH:7]=[C:8]([F:19])[C:9]=1[N:10]1[CH2:16][C:15](=[N:17][OH:18])[C:12]2([CH2:14][CH2:13]2)[CH2:11]1.[CH2:31](Br)[CH3:32]>CN(C=O)C>[F:3][C:4]1[CH:5]=[C:6]([N:20]2[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]2=[O:30])[CH:7]=[C:8]([F:19])[C:9]=1[N:10]1[CH2:16][C:15](=[N:17][O:18][CH2:31][CH3:32])[C:12]2([CH2:13][CH2:14]2)[CH2:11]1

Participants

Conditions

Temperature: 0 °C

Procedure

While being maintained at 0° C., KOH (0.13 g, 2.4 mmol) was added to a solution of the (S)—N-{{3-[3,5-difluoro-4-(7-hydroxydimono?-5-azaspiro[2,4]heptan-5-yl)phenyl]-2-oxo-5-oxazolidinyl}methyl}acetamide (0.8 g, 1.4 mmol) obtained in Example 3 in 10 mL of DMF, and then slowly droplets of ethyl bromide (0.4 mL, 5.6 mmol) were added with stirring for 3 hours. After the reaction terminated, the reaction mixture was poured into cold water and extracted with ethyl acetate. The organic phase was washed with water and brine and dehydrated over anhydrous magnesium sulfate. Purification through flash column chromatography (n-hexane/ethyl acetate=1:4) afforded the target compound in a white pure form (0.52 g).

Workup

customAfter the reaction terminated
additionthe reaction mixture was poured into cold water
extractionextracted with ethyl acetate
washThe organic phase was washed with water and brine
customPurification through flash column chromatography (n-hexane/ethyl acetate=1:4)
customafforded the target compound in a white pure form (0.52 g)

Sources & evidence

ORD record: ord-7cfb43ec44584a7cb75e1c7428cf5b31
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168797B2

Reaction notes

Loading…