Hydrochloric Acid → Benzyl((3S,4R)-1-(2,4-dimethoxybenzyl)-2-oxo-4-(2-oxoethyl)azetidin-3-yl)carbamate

HRID 708451Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][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/[CH:22]=[CH:23]/[O:24]C.Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:4]=1[CH2:5][N:6]1[C@H:7]([CH2:22][CH:23]=[O:24])[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:9]1=[O:10]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of benzyl ((2R,3S)-1-(2,4-dimethoxybenzyl)-2-((E)-2-methoxyvinyl)-4-oxoazetidin-3-yl)carbamate (1.58 g, 3.70 mmol) in dioxane (37 ml) was added HCl (7.4 ml, 7.4 mmol) and heated to 50° C. for 4 h. After cooling to rt, the reaction mixture was quenched with saturated NaHCO3 (aq) and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried with Na2SO4 and concentrated in vacuo. The crude residue was purified by silica gel chromatography (EtOAc-Heptane, 0-80%) to afford the title compound (0.89 g, 58%). LCMS: Rt=0.86 min, m/z=413.0 (M+1). Method 2m_acidic.

Workup

temperatureAfter cooling to rt
customthe reaction mixture was quenched with saturated NaHCO3 (aq)
extractionextracted with EtOAc (3×)
washThe combined organic layers were washed with brine
dry with materialdried with Na2SO4
concentrationconcentrated in vacuo
customThe crude residue was purified by silica gel chromatography (EtOAc-Heptane, 0-80%)

Sources & evidence

ORD record: ord-0baa36fd959647ee850049081d053cf6
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174978B2

Reaction notes

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