Methyl 2-(4-methylphenylsulfonamido)acetate → HCID 10335671, compound

HRID 2075285Notes

Reaction equation

HRID 2075285 reaction equation
C(O[C:5]([C:7]1[C:12]([CH2:13]O)=[CH:11][C:10]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:9][N:8]=1)=[O:6])(C)C.[CH3:23][O:24][C:25](=[O:38])[CH2:26][NH:27]S(C1C=CC(C)=CC=1)(=O)=O.C[O-].[Na+]>>[CH3:23][O:24][C:25]([C:26]1[C:5]([OH:6])=[C:7]2[C:12]([CH:11]=[C:10]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[CH:9]=[N:8]2)=[CH:13][N:27]=1)=[O:38]

Participants

4

Reactant 3

HCID 562880Methyl 2-(4-methylphenylsulfonamido)acetateHCID 10942334Sodium MethoxideHCID 59696379HCID 59696379, compound

Product 1

HCID 10335671HCID 10335671, compoundYield 83%

Procedure

After subjecting the above Compound 5 (59.0 g, 195 mmol) to Mitsunobu reaction with N-tosylglycine methyl ester according to the method described in Document (WO02/30930), ring-closure was caused with 1M sodium methoxide, to give 3-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxylic acid methyl ester 6 (50.3 g) in 83% yield.

Sources & evidence

ORD record
ord-7e281b90f09a4eae96ef954f5514be15
Source dataset
uspto-grants-2011_04
Patent number
US07919623B2

Reaction notes

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