Tetrahydrofuran → HCID 178520841, compound

HRID 984962Notes

Reaction equation

HRID 984962 reaction equation
[C:1]([NH:9][CH2:10][CH2:11][C:12]([NH:14][C@H:15]([C:22]([OH:24])=[O:23])[CH2:16][C:17]1[N:21]=[CH:20][NH:19][CH:18]=1)=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.O1[CH2:29][CH2:28][CH2:27][CH2:26]1.C(Br)(Br)(Br)[Br:31]>>[Br:31][CH2:26][CH2:27][CH2:28][CH2:29][O:23][C:22](=[O:24])[C@H:15]([CH2:16][C:17]1[N:21]=[CH:20][NH:19][CH:18]=1)[NH:14][C:12](=[O:13])[CH2:11][CH2:10][NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 11205Carbon tetrabromideHCID 178520840HCID 178520840, compound

Product 1

HCID 178520841HCID 178520841, compound

Procedure

To a solution of N-nicotinoyl-β-alanyl-(L)-histidine (9.9 g, 30.1 mmoles) in tetrahydrofuran (200 ml) triphenylphosphine (23.7 g, 90.3 mmoles) and carbon tetrabromide (28.85 g, 90.3 moles) are added under stirring. The reaction mixture is left under stirring at room temperature for 24 hours. Lastly the solvent is removed by evaporation at reduced pressure. The obtained crude product is purified by chromatography on silica gel column eluting with n-hexane/ethyle acetate 1/1. N-nicotinoyl-β-alanyl-(L)-histidine 4-bromobutyl ester is obtained.

Workup

  1. waitThe reaction mixture is left
  2. stirringunder stirring at room temperature for 24 hours
  3. customLastly the solvent is removed by evaporation at reduced pressure
  4. customThe obtained crude product
  5. customis purified by chromatography on silica gel column
  6. washeluting with n-hexane/ethyle acetate 1/1

Sources & evidence

ORD record
ord-0743f6c9942c45bd86eb924f0dd7b72d
Source dataset
uspto-grants-2005_03
Patent number
US06869974B1

Reaction notes

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