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Hydrochloric Acid → 5-(4-(2-((Tert-butoxycarbonylamino)methyl)-5-fluorobenzamido)-N-methylbutylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylic acid

HRID 455315
Notes
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Reaction equation

HRID 455315 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:52]=[CH:51][C:50]([F:53])=[CH:49][C:11]=1[C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][S:19]([N:22]([C:24]1[N:33]=[C:32]([C:34]([O:36]C)=[O:35])[C:31]([O:38][S:39]([C:42]2[CH:48]=[CH:47][C:45]([CH3:46])=[CH:44][CH:43]=2)(=[O:41])=[O:40])=[C:30]2[C:25]=1[CH:26]=[CH:27][CH:28]=[N:29]2)[CH3:23])(=[O:21])=[O:20])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-].[Li+].Cl>O.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:52]=[CH:51][C:50]([F:53])=[CH:49][C:11]=1[C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][S:19]([N:22]([C:24]1[N:33]=[C:32]([C:34]([OH:36])=[O:35])[C:31]([O:38][S:39]([C:42]2[CH:48]=[CH:47][C:45]([CH3:46])=[CH:44][CH:43]=2)(=[O:41])=[O:40])=[C:30]2[C:25]=1[CH:26]=[CH:27][CH:28]=[N:29]2)[CH3:23])(=[O:20])=[O:21])=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86667517Methyl 5-(4-(2-((tert-butoxycarbonylamino)methyl)-5-fluorobenzamido)-N-methylbutylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate

Product 1

HCID 86667518
5-(4-(2-((Tert-butoxycarbonylamino)methyl)-5-fluorobenzamido)-N-methylbutylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylic acid
Yield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 5-(4-(2-((tert-butoxycarbonylamino)methyl)-5-fluorobenzamido)-N-methylbutylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate (Example 3.3; 2.75 mmol) in a 1:1 mixture of THF and water (5.5 mL) was added lithium hydroxide (4.13 mmol) at room temperature. After the reaction was finished, ethyl acetate and water were added. The aquous layer was treated with HCl 1N until pH=5-6. The aqueous layer was extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated, to obtain the target material in 41% yield.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customto obtain the target material in 41% yield

Sources & evidence

ORD record
ord-d452a700b5fd4662bef4541eda2fe989
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08497270B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes