2-Butene, 1-bromo-3-methyl- → 3-[2-(S)-(4-chloro-benzyl)-5-methyl-hex-4-enoyl]-4-(R)-methy-5-(S)-phenyl-oxazolidin-2-one

HRID 1795182Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:12]2[C@H:16]([CH3:17])[C@H:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:14][C:13]2=[O:24])=[O:11])=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C@H:9]([CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])[C:10]([N:12]2[C@H:16]([CH3:17])[C@H:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[O:14][C:13]2=[O:24])=[O:11])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a cooled (−78° C.) solution of 3-[3-(4-chloro-phenyl)-propionyl]-4-(R)-methyl-5-(S)-phenyl-oxazolidin-2-one, 32, (500 mg, 1.46 mmol) in THF (15 mL) is added sodium bis(trimethylsilyl)-amide (1.75 mL, 1.0M solution in THF, 1.75 mmol). The resulting solution is stirred at −78° C. then 4-bromo-2-methyl-2-butene (0.20 mL, 1.75 mmol) is slowly added. The resulting solution is stirred at room temperature overnight, and the solvent removed under reduced pressure. The crude product is purified by preparative HPLC to afford 213 mg (36% yield) of the desired compound as a colorless oil. 1H NMR (CDCl3 300 MHz) δ 0.83 (d, J=6.6 Hz, 3H), 1.62 (s, 3H), 1.70 (s, 3H), 2.20–2.55 (m, 2H), 2.77–3.10 (m, 2H), 4.20–4.35 (m, 1H), 4.55–4.68 (m, 1H), 5.15–5.25 (m, 1H), 5.38 (d, J=7.2 Hz, 1H), 7.15–7.45 (m, 9H). MS (ESI) m/z 412 (M+H+)

Workup

stirringThe resulting solution is stirred at room temperature overnight
customthe solvent removed under reduced pressure
customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record: ord-a3cfe82d3dba45228b8d4461e6289bfe
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026335B2

Reaction notes

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