HCID 67344538, compound → HCID 55277838, compound

HRID 1629750Notes

Reaction equation

HRID 1629750 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:12][S@](C(C)(C)C)=O)[CH:9]([CH3:11])[CH3:10])=[CH:4][C:3]=1[CH3:19]>CO.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:12])[CH:9]([CH3:10])[CH3:11])=[CH:4][C:3]=1[CH3:19]

Participants

4

Reactant 1

HCID 67344538HCID 67344538, compound

Product 1

HCID 55277838HCID 55277838, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolvent

Procedure

A solution of intermediate INT 59 (330 mg, 1.09 mmol) in MeOH (8 mL) was treated with HCl (4 M in dioxane, 0.55 mL, 2.2 mmol) and stirred overnight. After evaporation of the solvents, a solid was obtained. The solid was then dissolved in 2 M HCl (30 mL) and washed with EtOAc. The aqueous layer was separated and the pH adjusted to about 11 using 2 M NaOH followed by extraction with CH2Cl2 (3×). The organic extracts were combined, dried over sodium sulfate, filtered and concentrated.

Workup

  1. customAfter evaporation of the solvents
  2. customa solid was obtained
  3. washwashed with EtOAc
  4. customThe aqueous layer was separated
  5. extractionfollowed by extraction with CH2Cl2 (3×)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-73c1bf2084894d0a89b35fe7dbcc7165
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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