Acetic Acid → Ethyl 6-(4-fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

HRID 1817302Notes

Reaction equation

HRID 1817302 reaction equation
CO.[CH3:3][Si](C=[N+]=[N-])(C)C.[F:10][C:11]1[CH:34]=[CH:33][C:14]([CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:21][CH:20]=[C:19]([OH:31])[C:18]=3[C:17]2=[O:32])=[CH:13][CH:12]=1.C(O)(=O)C>C(Cl)(Cl)Cl>[F:10][C:11]1[CH:34]=[CH:33][C:14]([CH2:15][N:16]2[CH2:25][CH2:24][C:23]3[C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:21][CH:20]=[C:19]([O:31][CH3:3])[C:18]=3[C:17]2=[O:32])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887Methanol2×HCID 167693Trimethylsilyldiazomethane2×HCID 69061030Ethyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

Product 1

HCID 69058090Ethyl 6-(4-fluorobenzyl)-4-methoxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of chloroform (10 mL) and methanol (10 mL) was added trimethylsilyl diazomethane (2.0 M in hexanes, 5 mL, 0.01 mole). After stirring for 10 minutes at room temperature, ethyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate (1.6 g, 3.5 mmol) in chloroform was added. After 7 hours, methanol (5 mL) and trimethylsilyl diazomethane (2.5 mL, 0.005 mole) was added to the reaction mixture. After 1 hour, glacial acetic acid (3 mL) was added with gas evolution observed. The solution was stirred for 0.5 hour. The product mixture was concentrated under vacuum. The residual material was subjected to column chromatography on silica gel eluting with 0-100% ethyl acetate in hexanes. The appropriate fractions were combined and concentrated to afford the title compound as a foam.

Workup

  1. waitAfter 7 hours
  2. waitAfter 1 hour
  3. stirringThe solution was stirred for 0.5 hour
  4. concentrationThe product mixture was concentrated under vacuum
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8ebc705357c0437f82017658c8347b56
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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