Chloroform → HCID 69022853, compound

HRID 495301Notes

Reaction equation

HRID 495301 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([C:20]2[O:21][C:22]([CH2:25][NH:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[CH:23][CH:24]=2)=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1.CN(C1C=CC=CN=1)C.[C:45](OC(=O)C)(=[O:47])[CH3:46].C(Cl)(Cl)Cl>ClCCl>[C:45]([N:26]([CH2:25][C:22]1[O:21][C:20]([C:6]2[C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][C:9]([O:11][CH2:12][O:13][CH3:14])=[CH:8][C:7]=2[CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:24][CH:23]=1)[CH2:27][CH2:28][CH2:29][N:30]1[CH2:31][CH2:32][O:33][CH2:34][CH2:35]1)(=[O:47])[CH3:46]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 23147227HCID 23147227, compound

Product 1

HCID 69022853HCID 69022853, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 3,5-bis(methoxymethoxy)-2-{5-[N-(3-morpholinopropyl)aminomethyl]furan-2-yl}phenylacetate (46 mg, 0.094 mmol) obtained in Example 247 was dissolved in dichloromethane (1.0 mL), and dimethylaminopyridine (20 mg, 0.16 mmol) and acetic anhydride (0.1 mL, 1.1 mmol) were added thereto and stirred for 20 hours. Chloroform was added to the reaction solution for liquid-liquid separation. The organic layer was washed with 2 mol/L hydrochloric acid, aqueous saturated carbonic acid solution and aqueous saturated sodium chloride solution in order, then dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through preparative thin-layer chromatography (methanol/chloroform=1/9) to obtain methyl 2-{5-[N-acetyl-N-(3-morpholinopropyl)aminomethyl]furan-2-yl}-3,5-bis(methoxymethoxy)phenylacetate (45 mg, 89%).

Workup

  1. washThe organic layer was washed with 2 mol/L hydrochloric acid, aqueous saturated carbonic acid solution and aqueous saturated sodium chloride solution in order
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe solvent was evaporated away under reduced pressure
  4. customThe resulting residue was purified through preparative thin-layer chromatography (methanol/chloroform=1/9)

Sources & evidence

ORD record
ord-484c05ff647040f29e7ac258f33cd30a
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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