Tetrahydrofuran → HCID 25009770, compound

HRID 84038Notes

Reaction equation

HRID 84038 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].C([O:9][C@@H:10]([CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:37]=NC=N[CH:41]=2)=[CH:32][CH:31]=1)[C@H:11]([CH2:15][CH2:16][N:17]1[C:22](=[O:23])[C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[N:19]=[N:18]1)[C:12]([OH:14])=[O:13])=O.O1C[CH2:45][CH2:44][CH2:43]1>CO>[OH:9][C@@H:10]([CH2:28][CH2:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]2[CH:41]=[CH:45][C:44]([O:4][CH3:1])=[CH:43][CH:37]=2)=[CH:34][CH:35]=1)[C@H:11]([CH2:15][CH2:16][N:17]1[C:22](=[O:23])[C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[N:19]=[N:18]1)[C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 86700980(2S,3S)-3-(formyloxy)-2-[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]-5-(4-pyrimidin-5-ylphenyl)pentanoic acid

Product 1

HCID 25009770HCID 25009770, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (0.151 g) was added to a solution of the compound obtained from step h above (0.5 g) in methanol (5 mL) and tetrahydrofuran (5 mL) at 0° C. The reaction mixture was stirred at room temperature for 3 hours. The solvents were evaporated and the residue was taken into water and ethyl acetate. The organic layer was washed with water and brine solution, and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to obtain a residue which was purified by preperative thin layer chromatography using 10% methanol in dichloromethane as eluent to afford the title compound (0.008 g).

Workup

  1. customat 0° C
  2. customThe solvents were evaporated
  3. washThe organic layer was washed with water and brine solution
  4. dry with materialdried over anhydrous sodium sulphate
  5. customThe solvent was evaporated under reduced pressure
  6. customto obtain a residue which
  7. customwas purified by preperative thin layer chromatography

Sources & evidence

ORD record
ord-c40046638ff648db8db62b9dbbd06e3a
Source dataset
uspto-grants-2014_09
Patent number
US08846910B2

Reaction notes

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