Dichloromethane methanol → HCID 57301135, compound

HRID 1030541Notes

Reaction equation

HRID 1030541 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@@H:15]([CH2:16][CH2:17][C:18]2[O:19]C=CC=2)[N:14]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:13]1=[O:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[OH:33].C(Cl)Cl>>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@@H:15]([CH2:16][CH2:17][C:18]([OH:33])=[O:19])[N:14]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[C:13]1=[O:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 21226129Dichloromethane methanolHCID 57219190HCID 57219190, compound

Product 1

HCID 57301135HCID 57301135, compoundYield 46%

Procedure

A solution of (±)-t-butyl 2-[cis-3-benzyloxycarbonylamino-4-(2-(2-furyl)ethyl)-2-oxoazetidin-1-yl]acetate (100 mg) and sudan red 7B (0.2 mg) in 6 mL of methanol-methylene chloride (1:1) was cooled to -78° C. Ozone/oxygen was bubbled in to the solution up to the endpoint of sudan red. The solution was allowed to warm to ambient temperature when 0.25N NaOH (1.87 mL) and 30% hydrogen peroxide (0.25 mL) were added. The solution was stirred for 2 hrs and was then diluted with H2O. The organic solvents were removed, and the aqueous solution was washed with ethyl acetate. The aqueous solution was layered with ethyl acetate and the pH of the mixture lowered to 3.7 with dilute hydrochloric acid. The ethyl acetate layer was washed (saturated NaCl), dried (NaSO4), and concentrated. The residue was crystallized from diethyl ether to provide the title compound (44 mg, 46% yield), mp 118°-120° C. Recrystallization from ethyl acetate-hexane provided colorless crystals of the analytical sample.

Workup

  1. customOzone/oxygen was bubbled in to the solution up to the endpoint of sudan red
  2. additionwere added
  3. additionwas then diluted with H2O
  4. customThe organic solvents were removed
  5. washthe aqueous solution was washed with ethyl acetate
  6. washThe ethyl acetate layer was washed (saturated NaCl)
  7. dry with materialdried (NaSO4)
  8. concentrationconcentrated
  9. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-250370774c974556ae47556238e7a00a
Source dataset
uspto-grants-1992_04
Patent number
US05106842

Reaction notes

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