Hydrochloric Acid → HCID 67820091, compound

HRID 327038Notes

Reaction equation

HRID 327038 reaction equation
OC(C(F)(F)F)=O.[NH2:8][N:9]=[CH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([NH:24][CH:25]([C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[CH2:26][C:27]([O:29]CC)=[O:28])=[O:23])=[CH:13][CH:12]=1.[Li+].[OH-].Cl>CO>[NH2:8][N:9]=[CH:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([NH:24][CH:25]([C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[CH2:26][C:27]([OH:29])=[O:28])=[O:23])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 131718271HCID 131718271, compound

Product 1

HCID 67820091HCID 67820091, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

ethyl β-[[[[4-[4-(aminoiminomethyl)phenyl]butyl]amino]carbonyl]amino]-3-pyridinepropanoate TFA (100 mg; 2 mmol), methanol (5ml), and 2N LiOH (5ml) were stirred for 30 min. The solution was acidified to pH=3 with 3N HCl and reduced to dryness on a rotary evaporator. The residue was dissolved in acetonitrile/water and purified by HPLC on a C-18 HPLC column (30cm×5cm). A gradient of 10 to 40% acetonitrile/water/ 0.05% TFA in 30 min. was used and the acid eluted at an acetonitrile concentration of 15%. Fractions containing the desired peak were lyophilized to give 70 mg of white solid. FAB-MS: MH+ =384.

Workup

  1. customreduced to dryness on a rotary evaporator
  2. dissolutionThe residue was dissolved in acetonitrile/water
  3. custompurified by HPLC on a C-18 HPLC column (30cm×5cm)
  4. washthe acid eluted at an acetonitrile concentration of 15%
  5. additionFractions containing the desired peak

Sources & evidence

ORD record
ord-0405ba30e21e4376868bd942bf5e1479
Source dataset
uspto-grants-1993_12
Patent number
US05272162

Reaction notes

Loading…