Sodium Hydroxide → HCID 22449527, compound

HRID 2186832Notes

Reaction equation

HRID 2186832 reaction equation
[C:1]([NH:4][CH:5]1[C:14](=[O:15])[C:13]2[C:8](=[C:9]([CH3:20])[CH:10]=[CH:11][C:12]=2[NH:16]C(=O)C)[S:7][CH2:6]1)(=[O:3])[CH3:2].[OH-].[Na+]>Cl>[C:1]([NH:4][CH:5]1[C:14](=[O:15])[C:13]2[C:8](=[C:9]([CH3:20])[CH:10]=[CH:11][C:12]=2[NH2:16])[S:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22449494HCID 22449494, compound

Product 1

HCID 22449527HCID 22449527, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

109 mg of the compound prepared in (1) above was added to 10 ml of 6 N hydrochloric acid, and the mixture was stirred at 90° C. for 20 minutes. After cooling, the mixture was alkalinized by the addition of sodium hydroxide and extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. The residue obtained after removal of the solvent was subjected to silica gel column chromatography using a chloroform-ethyl acetate (4:1) mixed solvent as an eluant to obtain fractions containing the target compound. The fractions were concentrated to produce 51 mg of the title compound. p NMR(CDCl3) δ: 2.09(3H, s), 2.16(3H, s), 2.98(1H, m), 3.60(1H, m), 4.6-5.0(1H, m), 6.33(1H, d, J=9 Hz), 7.02(1H, d, J=9 Hz).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with chloroform
  3. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  4. customThe residue obtained
  5. customafter removal of the solvent
  6. additionmixed solvent as an eluant
  7. customto obtain fractions
  8. additioncontaining the target compound
  9. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-3208333c8fe94f81b1ac8cc85e032d65
Source dataset
uspto-grants-2002_06
Patent number
US06407115B1

Reaction notes

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