Ethyl Acetate → HCID 69317929, compound

HRID 1393384Notes

Reaction equation

HRID 1393384 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:25])[C@H:6]([CH2:15][C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([OH:23])=[C:18]([CH3:24])[CH:17]=1)[NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].Cl[CH2:27][C:28]1[C:36]2[O:35][C:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[N:33][C:32]=2[CH:31]=[CH:30][CH:29]=1.C(OCC)(=O)C>CS(C)=O>[CH3:3][O:4][C:5](=[O:25])[C@H:6]([CH2:15][C:16]1[CH:17]=[C:18]([CH3:24])[C:19]([O:23][CH2:27][C:28]2[C:36]3[O:35][C:34]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[N:33][C:32]=3[CH:31]=[CH:30][CH:29]=2)=[C:20]([CH3:22])[CH:21]=1)[NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 23033902HCID 23033902, compoundHCID 69316816HCID 69316816, compound

Product 1

HCID 69317929HCID 69317929, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

60% Sodium hydride (20 mg, 0.495 mmol) was added to a solution of N-t-butoxycarbonyl-3,5-dimethyl-L-tyrosine methyl ester (160 mg, 0.495 mmol) in dimethyl sulfoxide (2 ml) at 18° C. and the mixture was stirred at the same temperature for 30 minutes. To the mixture was added dropwise a solution of 7-chloromethyl-2-phenylbenzoxazole (241 mg, 0.990 mmol) in dimethyl sulfoxide (3 ml) and the mixture was stirred at room temperature for 90 minutes. The reaction mixture was poured into a mixture of ice water and ethyl acetate and then extracted with ethyl acetate. The extract was washed with water and saturated saline solution in turn and dried. The solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=4) to give N-t-butoxycarbonyl-3,5-dimethyl-O-[(2-phenyl)benzoxazol-7-yl]methyl-L-tyrosine methyl ester (185 mg, 70%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 90 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and saturated saline solution in turn
  4. customdried
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=4)

Sources & evidence

ORD record
ord-ec34e01729bb498695f576f2583ee26c
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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