Potassium Carbonate → HCID 6319959, compound

HRID 746474Notes

Reaction equation

HRID 746474 reaction equation
Br[C:2]1([CH2:15][N:16]2[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:4][C:3]1([CH2:10][O:11]C(=O)C)[CH2:5][O:6]C(=O)C.C(=O)([O-])[O-].[K+].[K+].CO.O>CN(C)C=O>[OH:6][CH2:5][C:3]1([CH2:10][OH:11])[CH2:4]/[C:2]/1=[CH:15]/[N:16]1[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]1=[O:18].[OH:6][CH2:5][C:3]1([CH2:10][OH:11])[CH2:4]/[C:2]/1=[CH:15]\[N:16]1[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]1=[O:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22242641Methanol--water (1/1)HCID 66997785HCID 66997785, compound

Product 2

HCID 5271343HCID 5271343, compoundYield 36%HCID 6319959HCID 6319959, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of compound 18 (0.60 g, 1.49 mmol) from Example 17 and flame-dried potassium carbonate (616 mg, 4.47 mmol) in N,N-dimethylformamide (50 mL) was stirred at 100° C. under nitrogen for 3 h. After cooling, methanol-water (9:1, 10 mL) was added with stirring which was continued at room temperature for 1 h. The insoluble portion was filtered off and it was washed with N,N-dimethylformamide. The filtrate was evaporated in vacuo and the residue was chromatographed on a silica gel column which was first eluted with ethyl acetate and then dichloromethane-methanol (20:1) to give the Z-isomer 1f (70 mg, 38%) and E-isomer 2f (65 mg, 36%) as white solids.

Workup

  1. temperatureAfter cooling
  2. stirringwith stirring which
  3. waitwas continued at room temperature for 1 h
  4. filtrationThe insoluble portion was filtered off
  5. washit was washed with N,N-dimethylformamide
  6. customThe filtrate was evaporated in vacuo
  7. customthe residue was chromatographed on a silica gel column which
  8. washwas first eluted with ethyl acetate

Sources & evidence

ORD record
ord-38627d6cbb6e4924b2d924c1e84e9143
Source dataset
uspto-grants-2008_07
Patent number
US07393855B2

Reaction notes

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