Hydrochloric Acid → 4-[[N-(2-amino-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(3-amino-4-hydroxybenzyl)piperidine

HRID 279331Notes

Reaction equation

HRID 279331 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][C:38]=1[OH:39])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][NH:13][C:14](=[O:35])[CH2:15][NH:16][C:17](=[O:34])[C:18]2[CH:23]=[C:22]([F:24])[C:21]([F:25])=[CH:20][C:19]=2[NH:26]C(OC(C)(C)C)=O)[CH2:8][CH2:7]1.Cl>CO.O1CCOCC1>[NH2:26][C:19]1[CH:20]=[C:21]([F:25])[C:22]([F:24])=[CH:23][C:18]=1[C:17]([NH:16][CH2:15][C:14]([NH:13][CH2:12][CH:9]1[CH2:8][CH2:7][N:6]([CH2:5][C:4]2[CH:36]=[CH:37][C:38]([OH:39])=[C:2]([NH2:1])[CH:3]=2)[CH2:11][CH2:10]1)=[O:35])=[O:34]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 184262671-(3-amino-4-hydroxybenzyl)-4-[[N-(2-(tert-butoxycarbonylamino)-4,5-difluorobenzoyl)glycyl]aminomethyl]piperidine

Product 1

HCID 184261414-[[N-(2-amino-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(3-amino-4-hydroxybenzyl)piperidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-(3-amino-4-hydroxybenzyl)-4-[{N-(2-(tert-butoxycarbonylamino)-4,5-difluorobenzoyl)glycyl}aminomethyl]piperidine (20.0 mg, 0.035 mmol) in methanol (1 mL) was added 4 N HCl in dioxane (0.50 mL) and the solution was stirred at room temperature overnight. After the solution was concentrated, the residue was dissolved in methanol, loaded onto Varian™ SCX column, washed with CH3OH (5 mL×2), and eluted off using 2 N NH3 in CH3OH (5 mL). Concentration afforded 4-[{N-(2-amino-4,5-difluorobenzoyl)glycyl}aminomethyl]-1-(3-amino-4-hydroxybenzyl)piperidine (Compound No. 2141) (17.6 mg, quant.). The purity was determined by RPLC/MS (85%); ESI/MS m/e 448.3 (M++H, C22H27F2N5O3).

Workup

  1. concentrationAfter the solution was concentrated
  2. dissolutionthe residue was dissolved in methanol
  3. washwashed with CH3OH (5 mL×2)
  4. washeluted off
  5. concentrationConcentration

Sources & evidence

ORD record
ord-7d5cdda271a643c7b5c345a3db019112
Source dataset
uspto-grants-2002_03
Patent number
US06362177B1

Reaction notes

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