Hydrochloric Acid → HCID 69022700, compound

HRID 495303Notes

Reaction equation

HRID 495303 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[O:10][C:9]([C:11]2[C:16]([O:17]COC)=[CH:15][C:14]([O:21]COC)=[CH:13][C:12]=2[CH2:25][C:26]([O:28]C)=[O:27])=[CH:8][CH:7]=1)(=[O:3])[CH3:2].C(OC(=O)C)(=O)C.N1C=CC=CC=1.[OH-].[Na+].Cl>ClCCl.CO>[C:1]([NH:4][CH2:5][C:6]1[O:10][C:9]([C:11]2[C:16]([OH:17])=[CH:15][C:14]([OH:21])=[CH:13][C:12]=2[CH2:25][C:26]([OH:28])=[O:27])=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 69023344HCID 69023344, compound

Product 1

HCID 69022700HCID 69022700, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 2-[5-(N-acetylaminomethyl)furan-2-yl]-3,5-bis(methoxymethoxy)phenylacetate (45 mg, 0.15 mmol) obtained in Example 264 was dissolved in dichloromethane (1.0 mL), and acetic anhydride (0.20 mL, 2.12 mmol) and pyridine (0.20 mL, 2.5 mmol) were added thereto and stirred at room temperature for 3 hours. Methanol (5.0 mL) was added to the reaction solution, then stirred for 0.5 hours, and concentrated under reduced pressure. The resulting residue was dissolved in acetonitrile (1.0 mL), and aqueous 4 mol/L sodium hydroxide solution (1.0 mL, 4.0 mmol) was added thereto and stirred at 40° C. for 4 hours. 3 mol/L hydrochloric acid (3.0 mL) was added to the reaction solution, and concentrated under reduced pressure, and the resulting residue was purified through HP-20 (Mitsubishi Chemical Industry; water to acetonitrile/water=1/4) to obtain Compound 266 (23 mg, 23%).

Workup

  1. stirringstirred for 0.5 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in acetonitrile (1.0 mL)
  4. stirringstirred at 40° C. for 4 hours
  5. concentrationconcentrated under reduced pressure
  6. customthe resulting residue was purified through HP-20 (Mitsubishi Chemical Industry; water to acetonitrile/water=1/4)

Sources & evidence

ORD record
ord-19c2317e96d749fbb6158b3ebf9ce575
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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