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Acetic Acid → Methyl 5-(5-(tert-butoxycarbonylamino)-N-methylpentylsulfonamido)-8-hydroxy-1,6-naphthyridine-7-carboxylate

HRID 455308
Notes
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Reaction equation

HRID 455308 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14]([N:17]([C:19]1[N:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[C:26]([O:33]S(C2C=CC(C)=CC=2)(=O)=O)=[C:25]2[C:20]=1[CH:21]=[CH:22][CH:23]=[N:24]2)[CH3:18])(=[O:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].CO.C(O)(=O)C>CN(C=O)C.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14]([N:17]([C:19]1[N:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[C:26]([OH:33])=[C:25]2[C:20]=1[CH:21]=[CH:22][CH:23]=[N:24]2)[CH3:18])(=[O:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 10942334Sodium MethoxideHCID 86667514Methyl 5-(5-(tert-butoxycarbonylamino)-N-methylpentylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate

Product 1

HCID 67109690Methyl 5-(5-(tert-butoxycarbonylamino)-N-methylpentylsulfonamido)-8-hydroxy-1,6-naphthyridine-7-carboxylate
Yield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 5-(5-(tert-butoxycarbonylamino)-N-methylpentylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate (Example 2.1; 8.68 mmol) was dissolved in DMF (17 ml) at 40° C. and transferred to a 33% solution of NaOMe in MeOH (4.1 ml; 21.7 mmol) over 1-2 min at 25° C. The resulting yellow homogenous mixture was heated to 50° C. Mixture was cooled to 25° C. over 15 min and aged at 25° C. for 15 min. Acetic acid (1 ml) was added over 1 min, then water was added. The slurry was aged for 30 min and filtered. The filter cake was washed with water, and dried to give the target compound in 61% yield.

Workup

  1. temperatureMixture was cooled to 25° C. over 15 min
  2. waitThe slurry was aged for 30 min
  3. filtrationfiltered
  4. washThe filter cake was washed with water
  5. customdried
  6. customto give the target compound in 61% yield

Sources & evidence

ORD record
ord-b47920a914b14048869584783a2b898b
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08497270B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes