Hydrochloric Acid → HCID 55278770, compound

HRID 1629735Notes

Reaction equation

HRID 1629735 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C@H:9]([NH:11][S@](C(C)(C)C)=O)[CH3:10])=[CH:4][C:3]=1[CH3:18].Cl>CO>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C@H:9]([NH2:11])[CH3:10])=[CH:4][C:3]=1[CH3:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67346499HCID 67346499, compound

Product 1

HCID 55278770HCID 55278770, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of intermediate INT 40 (2.3 g, 8 mmol) in MeOH (50 mL) was treated with HCl (4 M in dioxane, 4 mL, 16 mmol) and stirred overnight. After evaporation of the solvents, a solid was obtained which was washed with Et2O. The solid was then dissolved in water, slightly acidified with 2 M HCl and washed with EtOAc. The aqueous layer was separated and the pH adjusted to about 11 using 2 M NaOH followed by extraction with Et2O (3×). The Et2O layers were combined, dried over sodium sulfate, filtered and concentrated.

Workup

  1. customAfter evaporation of the solvents
  2. customa solid was obtained which
  3. washwas washed with Et2O
  4. dissolutionThe solid was then dissolved in water
  5. washwashed with EtOAc
  6. customThe aqueous layer was separated
  7. extractionfollowed by extraction with Et2O (3×)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-0cb4e8b546ec4fceaa5554566090ae2a
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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