Hydrochloric Acid → HCID 68997123, compound

HRID 1909812Notes

Reaction equation

HRID 1909812 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:7][O:8][C:9]1[CH:21]=[CH:20][C:12]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:11][CH:10]=1.[OH-].[Na+].[C:24]([O:28]C)(=[O:27])[CH:25]=[CH2:26].Cl>O1CCOCC1.ClCCl>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[O:13][C:12]1[CH:20]=[CH:21][C:9]([O:8][CH2:7][CH:3]2[CH2:4][CH2:5][CH2:6][N:2]2[CH2:26][CH2:25][C:24]([OH:28])=[O:27])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 14798Sodium HydroxideHCID 68998830HCID 68998830, compound

Product 1

HCID 68997123HCID 68997123, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

The product from Example 167 (125 mg, 0.37 mmol) was treated with 20% NaOH (10 mL) and extracted with EtOAc, dried over Na2SO4 and dried down to give the free base. Dichloromethane (3 mL) and methyl acrylate (1 mL, 7 mmol) were added and the mixture was stirred at ambient temperature overnight. The reaction mixture was dried down to give oil. 4.0M HCl in dioxane was added and the mixture was stirred overnight at ambient temperature. The solvent was evaporated to give the title compound (61 mg, 57%); LC/MS; m/z 343 (M+H) 99%

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. customdried down
  4. customto give the free base
  5. customThe reaction mixture was dried down
  6. customto give oil
  7. stirringthe mixture was stirred overnight at ambient temperature
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d1e9bb9f0af742f88a4cf010ee040043
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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