Hydrochloric Acid → (2R,5R)-6-(allyloxy)-4-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxylic acid

HRID 627090Notes

Reaction equation

[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[C:7]([CH3:18])=[CH:8][C@H:9]2[C:14]([O:16]C)=[O:15])[CH:2]=[CH2:3].[OH-].[Li+].Cl>C1COCC1.O>[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[C:7]([CH3:18])=[CH:8][C@@H:9]2[C:14]([OH:16])=[O:15])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2S,5R)-methyl 6-(allyloxy)-4-methyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxylate (Intermediate 30, 0.479 g, 1.90 mmol) in THF (10 mL) and water (5 mL) at 0° C. was added lithium hydroxide (0.045 g, 1.90 mmol). The reaction was stirred at 0° C. for 2 hours. Another 0.5 eq lithium hydroxide was added. After 2 hours the reaction mixture was neutralized carefully with 1N HCl at 0° C. and the THF was evaporated. The aqueous was frozen and lyophilized to afford a light orange solid (0.464 g, 103% crude).

Workup

customthe THF was evaporated
temperatureThe aqueous was frozen
customto afford a light orange solid (0.464 g, 103% crude)

Sources & evidence

ORD record: ord-8497a4ea6a0e47579a832d4de00f286d
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309245B2

Reaction notes

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