Hydrochloric Acid → HCID 131719263, compound

HRID 1684642Notes

Reaction equation

HRID 1684642 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH:17]2[CH:13]([CH2:14][CH2:15][C:16]2=O)[CH:12]1[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](C1C=CC=CC=1[Se]C#N)([O-])=[O:26].C(P(CCCC)CCCC)CCC.OO.Cl>O1CCCC1.N1C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH:17]2[CH:13]([CH:14]([OH:26])[CH:15]=[CH:16]2)[CH:12]1[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 13831TributylphosphineHCID 1039312-Nitrophenyl selenocyanateHCID 54388940HCID 54388940, compound

Product 1

HCID 131719263HCID 131719263, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of the compound prepared as described in Example 3 (6.89 g) and 2-nitrophenyl selenocyanate (4.72 g) in tetrahydrofuran (100 ml)was cooled to about -20° C. under a nitrogen atmosphere. The cooled solution was treated with tributylphosphine (5.2 ml)in one portion. After one hour, the reaction solution was treated with pyridine (100 ml) and the resulting mixture allowed to warm to room temperature. The reaction was then treated with 30% hydrogen peroxide (35 ml). After an additional two hours, the reaction mixture was added to 1N hydrochloric acid (200 ml), and the title compound was extracted with diethyl ether. The diethyl ether extracts were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative HPLC, eluting with a linear gradient of hexane to hexane/ethyl acetate (1:1), to give 4.97 g of compound 7.

Workup

  1. customA solution of the compound prepared
  2. temperatureto warm to room temperature
  3. waitAfter an additional two hours
  4. extractionthe title compound was extracted with diethyl ether
  5. dry with materialThe diethyl ether extracts were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative HPLC
  8. washeluting with a linear gradient of hexane to hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-7c14a759f8e14ec481d18b0ba84cfba8
Source dataset
uspto-grants-1997_06
Patent number
US05641798

Reaction notes

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