Hexane → HCID 53664641, compound

HRID 1701668Notes

Reaction equation

HRID 1701668 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH2:15][N:14]([C:16](=[C:33]([CH3:35])[CH3:34])[C:17]([O:19]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:18])[C:13]1=[O:36])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCCCC>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH2:15][N:14]([C:16](=[C:33]([CH3:34])[CH3:35])[C:17]([OH:19])=[O:18])[C:13]1=[O:36])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8058HexaneHCID 54027933HCID 54027933, compound

Product 1

HCID 53664641HCID 53664641, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

Benzhydryl 2-(3-phenoxyacetamido-2-oxoazetidin-1-yl)-3-methyl-2-butenoate (100 mg) was dissolved in a mixture of 2 ml of anisole and 1 ml of trifluoroacetic acid at 0°. After 10 minutes 50 ml of hexane was added. The residue obtained by evaporating the solution in vacuo to dryness was taken up in ethyl acetate and the resulting solution was layered with water. After the pH of the aqueous layer was adjusted to 8.5, the aqueous layer was separated and layered with ethyl acetate. The pH of the aqueous layer was then adjusted to 2.5. The organic layer was separated, dried and evaporated to dryness in vacuo to provide 23 mg of the title product: nmr (CDCl3) δ 1.98 (s, 3, CH3), 2.17 (s, 3, CH3), 3.60 (m, 2, C4 --H), 4.98 (m, 1, C3 --H), 4.60 (s, 2, --OCH2CO), and 7.2 (b, 5, ArH).

Workup

  1. customThe residue obtained
  2. customby evaporating the solution in vacuo to dryness
  3. customthe aqueous layer was separated
  4. customThe organic layer was separated
  5. customdried
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-a49bb962d805441ab0af95d3355a0305
Source dataset
uspto-grants-1980_03
Patent number
US04195021

Reaction notes

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