Water → HCID 178525816, compound

HRID 84005Notes

Reaction equation

HRID 84005 reaction equation
[OH:1][C@H:2]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:29]=[N:30][C:31]([O:34]C)=[CH:32][CH:33]=2)=[CH:24][CH:23]=1)[C@H:3]([CH2:7][CH2:8][N:9]1[C:14](=[O:15])[C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]=[N:10]1)[C:4]([OH:6])=[O:5].B(Br)(Br)Br.C(OCC)(=O)C.O>C1(C)C=CC=CC=1>[OH:1][C@H:2]([CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:29]=[N:30][C:31]([OH:34])=[CH:32][CH:33]=2)=[CH:26][CH:27]=1)[C@H:3]([CH2:7][CH2:8][N:9]1[C:14](=[O:15])[C:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]=[N:10]1)[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 66671252(2S,3R)-3-hydroxy-5-[4-(6-methoxypyridin-3-yl)phenyl]-2-[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]pentanoic acid

Product 1

HCID 178525816HCID 178525816, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the compound obtained from Example 1A above (0.2 g) in dry toluene (5 mL), cooled to 78° C., boron tribromide (0.5 mL) was added and the contents were stirred at room temperature for 4 hours. Ethyl acetate and water were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain a residue which was purified by preparatory thin layer chromatography (2 mm thickness) using 15% methanol in dichloromethane as eluent to get the title compound (60 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customto obtain a residue which
  6. customwas purified by preparatory thin layer chromatography (2 mm thickness)

Sources & evidence

ORD record
ord-61578a13bfaf4fee816be46714fe234a
Source dataset
uspto-grants-2014_09
Patent number
US08846910B2

Reaction notes

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