Water → HCID 57742157, compound

HRID 1626884Notes

Reaction equation

HRID 1626884 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([OH: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[NH:13][C:23](=[S:24])[O: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 12370790HCID 12370790, compound

Product 1

HCID 57742157HCID 57742157, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Solution of 2-(4-Amino-3-hydroxy-phenyl)-propionic acid ethyl ester (570 mg) in DMF (5 mL) was added phenyl chlorothionoformate (563 mg in DMF), and DBU (829 mg, in DMF) at room temperature. The reaction mixture was stirred for 14 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=10:1 to 4:1) to afford the product as yellow oil. (90 mg, 13.2%)

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=10:1 to 4:1)

Sources & evidence

ORD record
ord-ccf80baed1e24da0a1ba1565c3ff6f85
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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