Hydrochloric Acid → HCID 131721668, compound

HRID 378129Notes

Reaction equation

HRID 378129 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].FC(F)(F)C(O)=O.N[C:13]1[CH:14]=[C:15]([C:19]([NH:21][CH2:22][C:23]([NH:25][CH:26]([C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)[CH2:27][C:28]([O:30]CC)=[O:29])=[O:24])=[O:20])[CH:16]=[CH:17][CH:18]=1.[OH-].[K+].C(O)(C(F)(F)F)=O.[ClH:48]>>[ClH:48].[NH2:1][C:2]([NH:4][C:17]1[CH:16]=[C:15]([C:19]([NH:21][CH2:22][C:23]([NH:25][CH:26]([C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)[CH2:27][C:28]([OH:30])=[O:29])=[O:24])=[O:20])[CH:14]=[CH:13][CH:18]=1)=[O:3]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1176UreaHCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 22608559HCID 22608559, compound

Product 1

HCID 131721668HCID 131721668, compound

Procedure

Urea (4 g) and ethyl β-[[2-[[(3-aminophenyl)-carbony]amino]acetyl]amino]pyridine-3-propanoate trifluoroacetate salt (4 g) were dissolved in 20% aqueous HCl (50 ml) and refluxed for 6 hours. The reaction was made basic with KOH (pH>12). After 4 hours the reaction was acidified with TFA and purified by HPLC (RP--CH3CN/H2O). The white solid was dissolved in 1:1 CH3CN:H2O (100 ml) and subjected to the resin exchange described in Example 43, Step C. Lyophilization gave the desired product (3.2 g). MS, 1H-NMR and CHNCl were consistent with the desired product.

Workup

  1. temperaturerefluxed for 6 hours
  2. custompurified by HPLC (RP--CH3CN/H2O)
  3. dissolutionThe white solid was dissolved in 1:1 CH3CN

Sources & evidence

ORD record
ord-ce74f22b3a5f48808f1fcbe9e1d31cfe
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

Loading…