Acetic Anhydride → HCID 67973349, compound

HRID 623884Notes

Reaction equation

HRID 623884 reaction equation
[C:1]([O:4]C(=O)C)(=[O:3])[CH3:2].[F:8][C:9]1[CH:10]=[C:11]([C:19]2[C:20]([CH3:34])=[CH:21][C:22]([O:25][CH2:26][C:27]([CH3:33])([CH3:32])[C:28]([O:30][CH3:31])=[O:29])=[N:23][CH:24]=2)[CH:12]=[CH:13][C:14]=1[C:15](=[NH:18])[NH:16]O>C(O)(=O)C>[C:1]([OH:4])(=[O:3])[CH3:2].[C:15]([C:14]1[CH:13]=[CH:12][C:11]([C:19]2[C:20]([CH3:34])=[CH:21][C:22]([O:25][CH2:26][C:27]([CH3:32])([CH3:33])[C:28]([O:30][CH3:31])=[O:29])=[N:23][CH:24]=2)=[CH:10][C:9]=1[F:8])(=[NH:16])[NH2:18]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178500416HCID 178500416, compound

Product 1

HCID 67973349HCID 67973349, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetic anhydride (1.62 mL) was added to an acetic acid (10 mL) solution containing methyl 3-({5-[3-fluoro-4-(N-hydroxycarbamimidoyl)phenyl]-4-methylpyridin-2-yl}-oxy)-2,2-dimethylpropanoate (3.65 g), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in methanol (30 mL), 10% palladium carbon (50%, 365 mg) was added to the resulting solution, and the mixture was stirred under hydrogen atmosphere at room temperature for 13 hours. The catalyst was filtered off by using a membrane filter, and the filtrate was concentrated under reduced pressure. Ether was added to the obtained residue, and the precipitated solid was collected by filtration, washed with ether and dried to obtain methyl 3-{[5-(4-carbamimidoyl-3-fluorophenyl)-4-methylpyridin-2-yl]oxy}-2,2-dimethylpropanoate acetic acid salt (2.45 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (30 mL)
  3. addition10% palladium carbon (50%, 365 mg) was added to the resulting solution
  4. stirringthe mixture was stirred under hydrogen atmosphere at room temperature for 13 hours
  5. filtrationThe catalyst was filtered off
  6. filtrationfilter
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. additionEther was added to the obtained residue
  9. filtrationthe precipitated solid was collected by filtration
  10. washwashed with ether
  11. customdried

Sources & evidence

ORD record
ord-1415e56ea5d4457d9727dcbf662d8200
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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