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

HRID 133614Notes

Reaction equation

HRID 133614 reaction equation
O1CCOCC1.Cl.[NH2:8][C:9]1[CH:10]=[C:11]([CH:43]=[CH:44][C:45]=1[OH:46])[CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][NH:20][C:21](=[O:42])[CH2:22][NH:23][C:24](=[O:41])[C:25]2[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:26]=2[NH:33]C(OC(C)(C)C)=O)[CH2:15][CH2:14]1>CO>[NH2:33][C:26]1[CH:27]=[C:28]([F:32])[C:29]([F:31])=[CH:30][C:25]=1[C:24]([NH:23][CH2:22][C:21]([NH:20][CH2:19][CH:16]1[CH2:15][CH2:14][N:13]([CH2:12][C:11]2[CH:43]=[CH:44][C:45]([OH:46])=[C:9]([NH2:8])[CH:10]=2)[CH2:18][CH2:17]1)=[O:42])=[O:41]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 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 1

HCID 887MethanolSolvent

Procedure

A 4 M dioxane solution of HCl (0.50 mL) was added to a methanol (1 mL) solution of 1-(3-amino-4-hydroxybenzyl)-4-[[N-(2-(tert-butoxycarbonylamino)-4,5-difluorobenzoyl)glycyl]aminomethyl]piperidine (20.0 mg, 0.035 mmol), and the resulting mixture was stirred at room temperature overnight and concentrated. The obtained residue was then dissolved in methanol, loaded onto a Varian™ SCX column, washed with methanol (5 mL×2), eluted with a 2 M methanol solution of NH3 (5 mL) and concentrated to thereby afford 4-[[N-(2-amino-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(3-amino-4-hydroxybenzyl)piperidine (Compd. No. 2141) (17.6 mg, quantitative). The purity was determined by RPLC/MS (85%). ESI/MS m/e 448.3 (M++H, C22H27F2N5O3).

Workup

  1. concentrationconcentrated
  2. dissolutionThe obtained residue was then dissolved in methanol
  3. washwashed with methanol (5 mL×2)
  4. washeluted with a 2 M methanol solution of NH3 (5 mL)
  5. concentrationconcentrated to thereby afford 4-[[N-(2-amino-4,5-difluorobenzoyl)glycyl]aminomethyl]-1-(3-amino-4-hydroxybenzyl)piperidine (Compd. No

Sources & evidence

ORD record
ord-e76649e97ecf49ed827c3b35c5a41ead
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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