HCID 86649304, compound → HCID 59627241, compound

HRID 1523243Notes

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of methyl (1S)-1-(4-bromophenyl)ethyl(3-((S)-tert-butylsulfinylimino)-3-(4-fluorophenyl)propyl)carbamate (200 mg, 0.4 mmol) in anhydrous THF (5 mL) was added 1M allylmagnesium bromide (1.2 mL, 1.2 mmol) at −78° C. The reaction mixture was stirred at −78° C. for 4 h and allowed to warm to rt. After stirring for 2 h at rt, the reaction mixture was quenched with satd aq NH4Cl and extracted with EtOAc (2×). The combined organic phases were dried, filtered and concentrated to give a residue, which was purified by TLC to provide methyl (S)-1-(4-bromophenyl)ethyl((S)-3-((S)-1,1-dimethylethylsulfinamido)-3-(4-fluorophenyl)hex-5-enyl)carbamate (96 mg, 45%). 1H NMR (CD3OD): 1.28 (m, 9H), 1.48 (m, 3H), 2.10 (m, 1H), 2.30 (m, 1H), 2.72 (m, 4H), 3.66 (m, 3H), 5.08 (m, 2H), 5.40 (m, 2H), 7.10 (m, 4H), 7.32 (m, 2H), 7.50 (m, 2H).

Workup

temperatureto warm to rt
stirringAfter stirring for 2 h at rt
customthe reaction mixture was quenched with satd aq NH4Cl
extractionextracted with EtOAc (2×)
customThe combined organic phases were dried
filtrationfiltered
concentrationconcentrated
customto give a residue, which
customwas purified by TLC

Sources & evidence

ORD record: ord-295d75cae01c4fd4bd571e1356b373fb
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079861B2

Reaction notes

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