Methanesulfonyl chloride → ((2S,3S)-3-(((benzyloxy)carbonyl)amino)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-2-yl)methyl methanesulfonate

HRID 708312Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of benzyl ((2S,3S)-1-(2,4-dimethoxybenzyl)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamate (5.37 g, 13.41 mmol) and TEA (3.72 mL, 26.8 mmol) in DCM at 0° C. was added MsCl (1.15 mL, 14.75 mmol). After stirring at 0° C. for 1 h, it was diluted with water/DCM and the layers were separated. The aqueous layer was extracted with DCM (2×) and the combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude residue was taken up in toluene and concentrated (2×), affording the title compound as an off white solid. It was used as such in subsequent reactions. LCMS: Rt=0.86 min, m/z=479.2 (M+1) Method 2m_acidic.

Workup

customthe layers were separated
extractionThe aqueous layer was extracted with DCM (2×)
washthe combined organic layers were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
concentrationconcentrated (2×)

Sources & evidence

ORD record: ord-18c2a06e464b49b5b38ccdae62e4aaf3
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174978B2

Reaction notes

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