Triethylamine → HCID 22013852, compound

HRID 1532743Notes

Reaction equation

HRID 1532743 reaction equation
[OH:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[CH:9][CH:8]=1)[C:3]([NH2:5])=[O:4].C(N(CC)CC)C.[C:35]([O:38][CH2:39]C)(=[O:37])C>ClCCl.O1CCCC1>[CH3:39][O:38][C:35]([O:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:19][C:20]=2[CH3:21])=[CH:9][CH:8]=1)[C:3]([NH2:5])=[O:4])=[O:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 22013856HCID 22013856, compound

Product 1

HCID 22013852HCID 22013852, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a solution of 2-hydroxy-3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionamide (550 mg, 1.50 mmol) obtained in Example 36 in dichloromethane-tetrahydrofuran (1:1, 50 ml) was added equivalent of methyl chlorofornate and triethylamine under ice-cooling until the reaction completed. The mixture was stirred for 1 hr, and the reaction mixture was diluted with ethyl acetate (100 ml) and washed successively with saturated brine, 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine. The mixture was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent; dichloromethane:methanol=98:2) to give the title compound (110 mg, yield 17%) as a white solid.

Workup

  1. temperaturecooling until the reaction
  2. washwashed successively with saturated brine, 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialThe mixture was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (developing solvent; dichloromethane:methanol=98:2)

Sources & evidence

ORD record
ord-eb4dd5e7c6334ffb914118d75bd75249
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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