Hydrazine hydrate (1:1) → HCID 10914026, compound

HRID 891280Notes

Reaction equation

HRID 891280 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:13]([C:16]2[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=2)[CH:14]=O)[C:9](OC)=[O:10])=[CH:4][CH:3]=1.O.[NH2:25][NH2:26]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:13]([C:16]3[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=3)[CH:14]=[N:26][NH:25][C:9]2=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10903700HCID 10903700, compound

Product 1

HCID 10914026HCID 10914026, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The aldehyde-ester, hydrate, and hydroxy lactone from Example 16 (0.10 g, 3 mmol), were dissolved in 100 mL of ethanol. This solution was treated with hydrazine monohydrate (0.15 mL, 30 mmol) and the resulting solution was stirred at reflux in a Soxhelet apparatus containing molcular sieves. After 18 hours, the reaction mixture was cooled and the volatile materials removed under reduced pressure. The residue was partitioned between ethyl acetate and aqueous HCl. The aqueous layer was washed twice with ethyl acetate. The combined organic extracts were washed twice with brine, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (4:1 hexanes/ethyl acetate) to obtain the title compound (yield: 50 mg, 53%). 1H NMR (300 MHz, CDCl3) δ 2.46 (s, 3H), 3.75 (d, J=12 Hz, 1H), 3.87 (d, J=12 Hz, 1H), 6.93-7.08 (m, 6H), 7.16 (d, J=9 Hz, 2H), 8.71 (s(br), 1H). MS (DCI/NH3) m/z 315 (M+H)+ and m/z 332 (M+NH4)+.

Workup

  1. temperatureat reflux in a Soxhelet apparatus
  2. additioncontaining molcular sieves
  3. temperaturethe reaction mixture was cooled
  4. customthe volatile materials removed under reduced pressure
  5. customThe residue was partitioned between ethyl acetate and aqueous HCl
  6. washThe aqueous layer was washed twice with ethyl acetate
  7. washThe combined organic extracts were washed twice with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customthe residue was purified by column chromatography (4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-f11ee3a3841040ba9b4f29389c5f9e8b
Source dataset
uspto-grants-2006_02
Patent number
US07001895B2

Reaction notes

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