HCID 18630005, compound → HCID 18630090, compound

HRID 1458088Notes

Reaction equation

HRID 1458088 reaction equation
[CH2:1]([N:3]([CH2:17][O:18]C)[C:4](=[O:16])[C:5]1[C:10]([Si:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:15])[CH3:2]>C(#N)C.Cl>[CH2:1]([N:3]([CH2:17][OH:18])[C:4](=[O:16])[C:5]1[C:10]([Si:11]([CH3:12])([CH3:13])[CH3:14])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:15])[CH3:2]

Participants

4

Reactant 1

HCID 18630005HCID 18630005, compound

Product 1

HCID 18630090HCID 18630090, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

The compound of Example 127 (0.80 g, 2.9 mmol) was refluxed in a mixture of acetonitrile (20 mL) and 2N HCl (20 mL). Within 2 h the reaction was complete by GLC, add was cooled and partitioned between ether and water. The ether phase was concentrated and purified by RC with 1:4 ethyl acetate/hexanes, then recrystallized from hexanes to give 160 mg of the title compound as a solid, a 21% yield.

Workup

  1. additionadd
  2. temperaturewas cooled
  3. custompartitioned between ether and water
  4. concentrationThe ether phase was concentrated
  5. custompurified by RC with 1:4 ethyl acetate/hexanes
  6. customrecrystallized from hexanes

Sources & evidence

ORD record
ord-509937c9890f405694ff27646556a88c
Source dataset
uspto-grants-1998_12
Patent number
US05849723

Reaction notes

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