Toluene → N-[4-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl)-2(R),3(S)-dimethylbutanoyl]-4(R)-isopropyl-2-oxazolidinone

HRID 1683992Notes

Reaction equation

[Br:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]([CH3:32])[CH2:20][C:21]([N:23]3[C@H:27]([CH:28]([CH3:30])[CH3:29])[CH2:26][O:25][C:24]3=[O:31])=[O:22])=[C:8]2[CH3:33])=[CH:4][CH:3]=1.[CH3:36][Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C)C=CC=CC=1.CI>C1COCC1>[Br:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][C@H:19]([CH3:32])[C@@H:20]([CH3:36])[C:21]([N:23]3[C@H:27]([CH:28]([CH3:29])[CH3:30])[CH2:26][O:25][C:24]3=[O:31])=[O:22])=[C:8]2[CH3:33])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -40 °C

Procedure

To the imide of Example 7, Step 7, isomer A (200 mg, 0.369 mmol) dissolved in THF (2.0 mL) at -78° C. was added a solution of KHMDS (0.5 mL) in toluene (1.10 mL, 0,660 mmol). The temperature was then increased slowly to -40° C. To the mixture recooled at -78° C. was added MeI (100 mL). The temperature was allowed to wam slowly to -40° and the reaction was quenched by the addition of 25% aqueous solution of NH4OAc. The mixture was extracted with EtOAc, dried over Na2SO4, evaporated in vacuo and purified by flash chromatography (20% EtOAc in hexane) to afford the title product (100 mg).

Workup

customrecooled at -78° C.
customto wam slowly to -40°
customthe reaction was quenched by the addition of 25% aqueous solution of NH4OAc
extractionThe mixture was extracted with EtOAc
dry with materialdried over Na2SO4
customevaporated in vacuo
custompurified by flash chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record: ord-898c1d2116914a968fb1578d7de577dc
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639780

Reaction notes

Loading…