Hydrochloric Acid → HCID 22346259, compound

HRID 897307Notes

Reaction equation

HRID 897307 reaction equation
[C:1]([O:9][C:10]1[C:19]2[N:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13](=[O:20])[NH:12][C:11]=1[C:21]([O:23][CH3:24])=[O:22])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[CH2:26][C:27]([N:29]([CH3:31])[CH3:30])=[O:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.Cl>C1COCC1>[C:1]([O:9][C:10]1[C:11]([C:21]([O:23][CH3:24])=[O:22])=[N:12][C:13]([O:20][CH2:26][C:27]([N:29]([CH3:31])[CH3:30])=[O:28])=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 128746822-Hydroxy-N,N-dimethylacetamideHCID 22346242HCID 22346242, compound

Product 1

HCID 22346259HCID 22346259, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0° C.) suspension of methyl 8-(benzoyloxy)-5-oxo-5,6-dihydro[1,6]-naphthyridine-7-carboxylate (3.24 g, 10 mmol), 2-hydroxy-N,N-dimethylacetamide (1.13 g, 11 mmol), and triphenylphosphine (5.24 g, 20 mmol) in THF (100 mL), diethyl azodicarboxylate (3.1 mL, 19.6 mmol) was added over a period of 3 minutes. The resultant mixture was stirred at room temperature for two days. The product mixture was treated with 1 M aq HCl and extracted with methylene chloride. The organic extract was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residual oil was subject to column chromatography on silica gel eluting with 1-2% methanol in ethyl acetate. Collection and concentration of the appropriate fractions provided the slower eluting o-alkylated isomer as white solid.

Workup

  1. additionwas added over a period of 3 minutes
  2. extractionextracted with methylene chloride
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customCollection and concentration of the appropriate fractions
  8. customprovided the
  9. washslower eluting o-alkylated isomer as white solid

Sources & evidence

ORD record
ord-30a58f4c74034d97a99bc82c01f34fe5
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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