Potassium Hydroxide → HCID 90411382, compound

HRID 627064Notes

Reaction equation

HRID 627064 reaction equation
C([O:3][C:4]([C:6]1[NH:23][C:9]2[C:10]3[CH2:11][CH2:12][N:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:15][C:16]=3[S:17][C:8]=2[CH:7]=1)=[O:5])C.[OH-].[K+]>CCO>[CH2:21]([O:20][C:18]([N:13]1[CH2:12][CH2:11][C:10]2[C:9]3[NH:23][C:6]([C:4]([OH:5])=[O:3])=[CH:7][C:8]=3[S:17][C:16]=2[CH2:15][CH2:14]1)=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 90411003HCID 90411003, compound

Product 1

HCID 90411382HCID 90411382, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of the product from step (e) (3.45 g, 10.26 mmol) in EtOH (120 ml) was added 2M KOH (50 ml). The reaction mixture was heated to 50° C. for 6 hours and then allowed to cool to RT. The reaction mixture was then stirred at RT for an additional 12 hours. The MeOH was then evaporated in vacuo and the remaining aqueous mixture was diluted with additional water (50 ml). The aqueous mixture was washed with EtOAc (2×). The aqueous mixture was then acidified with 2M HCl to pH 2 and extracted with DCM (3×). The combined DCM extracts were dried (Na2SO4), decanted, and solvent evaporated in vacuo to give the sub-titled compound as a tan solid (3.0 g) that was used without further purification. MS: ESI (positive): 308 (M+H), ESI (negative): 307 (M+H).

Workup

  1. temperatureto cool to RT
  2. customThe MeOH was then evaporated in vacuo
  3. additionthe remaining aqueous mixture was diluted with additional water (50 ml)
  4. washThe aqueous mixture was washed with EtOAc (2×)
  5. extractionextracted with DCM (3×)
  6. dry with materialThe combined DCM extracts were dried (Na2SO4)
  7. customdecanted
  8. customsolvent evaporated in vacuo

Sources & evidence

ORD record
ord-8497785fc3f5439884fcecd76f335407
Source dataset
uspto-grants-2016_04
Patent number
US09309262B2

Reaction notes

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