Potassium Carbonate → HCID 67110418, compound

HRID 455299Notes

Reaction equation

HRID 455299 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[F:11][C:12]1[CH:26]=[CH:25][C:15]([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[C:14]([OH:27])[CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[C:20]([O:19][C:18]([NH:17][CH2:16][C:15]1[CH:25]=[CH:26][C:12]([F:11])=[CH:13][C:14]=1[O:27][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:24])([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 84580Ethyl 5-bromovalerate2×HCID 67109671HCID 67109671, compound

Product 1

HCID 67110418HCID 67110418, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 5-bromopentanoate (14.9 mmol) was added dropwise over 15 minutes to a mixture of tert-butyl 4-fluoro-2-hydroxybenzylcarbamate (Example 15; 12.4 mmol) and potassium carbonate (16.1 mmol) in DMA (37 ml). The reaction was heated at 60° C. for 4 hours, followed by the addition of another amount of ethyl 5-bromopentanoate (4.5 mmol) and potassium carbonate (4.8 mmol) and heating at 60° C. for 2 hours. The solvent was evaporated. The residue was taken up in AcOEt and filtered. The filtrate was washed with AcOEt (×3) and concentrated in vacuo. The residue was purified by column chromategraphy over SiO2 (Hexanes/AcOEt, 8/1, v/v) to afford the target compound (4.1 gr, 96% purity).

Workup

  1. temperatureheating at 60° C. for 2 hours
  2. customThe solvent was evaporated
  3. filtrationfiltered
  4. washThe filtrate was washed with AcOEt (×3)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromategraphy over SiO2 (Hexanes/AcOEt, 8/1
  7. customv/v) to afford the target compound (4.1 gr, 96% purity)

Sources & evidence

ORD record
ord-819be190666b4bfb824dfb09ba44b6a0
Source dataset
uspto-grants-2013_07
Patent number
US08497270B2

Reaction notes

Loading…