Hydrochloric Acid → 2-((8-(Benzyloxy)-5-(6-(tert-butoxycarbonylamino)hexylamino)-1,6-naphthyridine-7-carboxamido)methyl)-5-fluorobenzoic acid

HRID 455307Notes

Reaction equation

HRID 455307 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:34]([NH:36][CH2:37][C:38]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][C:39]=2[C:40]([O:42]CC)=[O:41])=[O:35])=[N:11][C:12]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C>[CH2:1]([O:8][C:9]1[C:10]([C:34]([NH:36][CH2:37][C:38]2[CH:48]=[CH:47][C:46]([F:49])=[CH:45][C:39]=2[C:40]([OH:42])=[O:41])=[O:35])=[N:11][C:12]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68009450Ethyl 2-((8-(benzyloxy)-5-(6-(tert-butoxycarbonylamino)hexylamino)-1,6-naphthyridine-7-carboxamido)methyl)-5-fluorobenzoate

Product 1

HCID 671097012-((8-(Benzyloxy)-5-(6-(tert-butoxycarbonylamino)hexylamino)-1,6-naphthyridine-7-carboxamido)methyl)-5-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-((8-(benzyloxy)-5-(6-(tert-butoxycarbonylamino)hexylamino)-1,6-naphthyridine-7-carboxamido)methyl)-5-fluorobenzoate (Example 1.3; 0.64 g; 0.96 mmol) was dissolved in ethanol (4 ml). A solution of 1N NaOH (1.5 ml) was added at room temperature. After completion of the reaction, HCl 1 N was added until pH=2-3 was reached. The solvent was evaporated under pressure. The residue was taken-up in EtOAc and washed with H2O and brine. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. Yield: 0.592 g (96%; used in next reaction step, without further purification).

Workup

  1. additionwas added until pH=2-3
  2. customThe solvent was evaporated under pressure
  3. washwashed with H2O and brine
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customYield: 0.592 g (96%; used in next reaction step, without further purification)

Sources & evidence

ORD record
ord-918c2e7dd92b4cb9b81eba104e809140
Source dataset
uspto-grants-2013_07
Patent number
US08497270B2

Reaction notes

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