Acetic Acid → Methyl 5-(1,1-dioxido-1,2-thiazinan-2-yl)-8-hydroxy-1,6-naphthyridine-7-carboxylate

HRID 897366Notes

Reaction equation

HRID 897366 reaction equation
[O:1]=[S:2]1(=[O:33])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[N:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[C:15]([O:22]S(C2C=CC(C)=CC=2)(=O)=O)=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2.C[O-].[Na+].C(O)(=O)C.O>CN(C=O)C>[O:33]=[S:2]1(=[O:1])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[N:17]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[C:15]([OH:22])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 10942334Sodium MethoxideHCID 11386323Methyl 5-(1,1-dioxido-1,2-thiazinan-2-yl)-8-{[(4-methylphenyl)sulfonyl]oxy}-1,6-naphthyridine-7-carboxylate

Product 1

HCID 11325194Methyl 5-(1,1-dioxido-1,2-thiazinan-2-yl)-8-hydroxy-1,6-naphthyridine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 5-(1,1-dioxido-1,2-thiazinan-2-yl)-8-{[(4-methylphenyl)sulfonyl]oxy}-1,6-naphthyridine-7-carboxylate (6.0 g, 12.2 mmol) in DMF (50 mL) under nitrogen at zero degrees C. was added sodium methoxide (49.40 mL, 24.70 mmol, 0.5 M in Methanol). The cold solution was allowed to stir for one hour. Acetic acid (1.64 mL, 27.4 mmol) was added followed by water to precipitate the product. The mixture was allowed to stand for one hour. The crude reaction was filtered and the solids were washed with 1:1 methanol:water and dried in vacuo to afford the desired product.

Workup

  1. customat zero degrees C
  2. customto precipitate the product
  3. waitto stand for one hour
  4. customThe crude reaction
  5. filtrationwas filtered
  6. washthe solids were washed with 1:1 methanol
  7. dry with materialwater and dried in vacuo

Sources & evidence

ORD record
ord-aa9a700a319545779d6e56ebf1fcabe1
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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