Water → HCID 22013867, compound

HRID 1532740Notes

Reaction equation

HRID 1532740 reaction equation
[H-].[Na+].[H][H].C1(C)C=CC(S([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])(=O)=O)=CC=1.[OH2:30].[C:31]([O:34][CH2:35][CH3:36])(=[O:33])[CH3:32]>CCCCCC.CN(C)C=O>[C:17]([NH:18][CH:32]([CH2:19][C:23]1[CH:28]=[CH:27][C:26]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[O:20][C:21]=2[CH3:22])=[CH:25][CH:24]=1)[C:31]([O:34][CH2:35][CH3:36])=[O:33])(=[O:30])[CH3:16]

Participants

8

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 120517392-(5-Methyl-2-phenyloxazol-4-yl)ethyl 4-methylbenzenesulfonateHCID 178418361HCID 178418361, compound

Product 1

HCID 22013867HCID 22013867, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydride (60% in oil, 440 mg, 11.0 mmol) was washed twice with n-hexane (5 ml) under a nitrogen atmosphere, and suspended in N,N-dimethylformamide (50 ml) and ice-cooled. To this suspension was added ethyl N-acetyl-L-tyrosine ester (2.51 g, 10.0 mmol) over 15 min. Ten minutes later when hydrogen bubbling ended, a solution of 2-(5-methyl-2-phenyl-4-oxazolyl)ethyl p-toluenesulfonate (3.57 g, 10.0 mmol) in N,N-dimethylformamide (50 ml) was added. The mixture was stirred at 80° C. for 3 hr, and water (50 ml) and ethyl acetate (100 ml×2) were added for partition. The obtained organic layer was washed with saturated brine (100 ml), 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 (1.63 g, yield 37%) as a white solid.

Workup

  1. temperatureice-cooled
  2. customfor partition
  3. washThe obtained organic layer was washed with saturated brine (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (developing solvent; dichloromethane:methanol=98:2)

Sources & evidence

ORD record
ord-ab95d491c880408ab9b1fc146f1b27d2
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

Loading…