Water → Ethyl 2-(2-thioxo-2,3-dihydrobenzoxazol-5-yl)propionate

HRID 1626874Notes

Reaction equation

HRID 1626874 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([NH2:14])[CH:8]=1)[CH3:6])[CH3:2].C1C=CC(O[C:23](Cl)=[S:24])=CC=1.C1CCN2C(=NCCC2)CC1.O>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]2[O:13][C:23](=[S:24])[NH:14][C:9]=2[CH:8]=1)[CH3:6])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 70498Phenyl thioxochloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 12202638Ethyl 3-amino-4-hydroxy-phenyl-propionate

Product 1

HCID 20319623Ethyl 2-(2-thioxo-2,3-dihydrobenzoxazol-5-yl)propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(3-amino-4-hydroxy-phenyl)-propionic acid ethyl ester (370 mg) in DMF (2 mL) was added phenyl chlorothionoformate (380 mg in DMF), and DBU (540 mg, in DMF) at room temperature. The reaction mixture was stirred for 16 h at room temperature and water was added to this mixture. The resulting mixture was extracted with ethyl ether. The combined organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was chromatographed on silica gel (n-Hex:EtOAc=4:1) to afford the product as white solid. (130 mg, 29.2%)

Workup

  1. extractionThe resulting mixture was extracted with ethyl ether
  2. dry with materialThe combined organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was chromatographed on silica gel (n-Hex:EtOAc=4:1)

Sources & evidence

ORD record
ord-07d64ba52c3943bfafd556e77573f5a3
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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