Trifluoroacetic acid → Methyl 5-(4-amino-N-methylbutylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate

HRID 455313Notes

Reaction equation

HRID 455313 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][S:13]([N:16]([C:18]1[N:27]=[C:26]([C:28]([O:30][CH3:31])=[O:29])[C:25]([O:32][S:33]([C:36]2[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=2)(=[O:35])=[O:34])=[C:24]2[C:19]=1[CH:20]=[CH:21][CH:22]=[N:23]2)[CH3:17])(=[O:15])=[O:14])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][S:13]([N:16]([C:18]1[N:27]=[C:26]([C:28]([O:30][CH3:31])=[O:29])[C:25]([O:32][S:33]([C:36]2[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=2)(=[O:34])=[O:35])=[C:24]2[C:19]=1[CH:20]=[CH:21][CH:22]=[N:23]2)[CH3:17])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86667515Methyl 5-(4-(tert-butoxycarbonylamino)-N-methylbutylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate

Product 1

HCID 86667516Methyl 5-(4-amino-N-methylbutylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 5-(4-(tert-butoxycarbonylamino)-N-methylbutylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate (Example 3.1; 5.52 mmol) in dichloro methane (5 mL) was added trifluoro acetic acid (5 mL) at 0° C. After addition the reaction was warmed to room temperature. The solvent was evaporated and the residue was co-evaporated with toluene (3×). The resulting residue was dried under vacuum and used in the next step (Example 3.3) without further purification.

Workup

  1. additionAfter addition the reaction
  2. customThe solvent was evaporated
  3. customThe resulting residue was dried under vacuum
  4. customused in the next step (Example 3.3) without further purification

Sources & evidence

ORD record
ord-89da1d83e28a4194b21443cd893bc5e9
Source dataset
uspto-grants-2013_07
Patent number
US08497270B2

Reaction notes

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