Ethanol → HCID 131722875, compound

HRID 379076Notes

Reaction equation

HRID 379076 reaction equation
[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:22]([CH2:24]Br)=[O:23])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH2:34]([OH:36])[CH3:35]>>[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:22]([CH2:24][O:36][CH2:34][CH3:35])=[O:23])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 522689Potassium FluorideHCID 131722876HCID 131722876, compound

Product 1

HCID 131722875HCID 131722875, compound

Procedure

In a 100 ml round bottom flask equipped with an argon line was placed Nu-Phe-HPhe-CH2-Br (300 mg, 0.582 mmol), potassium fluoride (150 mg, 2.4 mmol), and potassium carbonate (150 mg, 1.2 mmol), and 8 ml of 200 proof ethanol. The reaction was stirred 3 hours, filtered and the solvents were removed under vacuum and the residue chromatographed on a short silica gel column (CHCl3:MLEOH 95:5) and then recrystallized from ether.

Workup

  1. customIn a 100 ml round bottom flask equipped with an argon line
  2. filtrationfiltered
  3. customthe solvents were removed under vacuum
  4. customthe residue chromatographed on a short silica gel column (CHCl3:MLEOH 95:5)
  5. customrecrystallized from ether

Sources & evidence

ORD record
ord-4b0c1d50da62453a8d5ae78a33a5ea29
Source dataset
uspto-grants-2001_10
Patent number
US06297277B1

Reaction notes

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