Tetrahydrofuran → HCID 178520841, compound

HRID 2224038Notes

Reaction equation

HRID 2224038 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 mmoles) 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/ethyl 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/ethyl acetate 1/1

Sources & evidence

ORD record
ord-81ca109d78ba4b56ad7e4a3d05ed570c
Source dataset
uspto-grants-2008_05
Patent number
US07378412B2

Reaction notes

Loading…