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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1436884Generated: November 2, 2026

5-(Tert-butyloxycarbonyl)-2-(4-fluorobenzyl)-8-hydroxy-6-methyl-2,3,4,4a,5,6-hexahydro-2,6-naphthyridine-1,7-dione → 2-(4-Fluorobenzyl)-8-hydroxy-6-methyl-2,3,4,4a,5,6-hexahydro-2,6-naphthyridine-1,7-dione-5-carboxylic acid

https://huagongshe.com/reaction/1436884

Reaction equation

Participants

RoleNameHCIDCharge
Reactant5-(Tert-butyloxycarbonyl)-2-(4-fluorobenzyl)-8-hydroxy-6-methyl-2,3,4,4a,5,6-hexahydro-2,6-naphthyridine-1,7-dioneHCID 54713757—
SolventDichloromethaneHCID 6344—
SolventTrifluoroacetic acidHCID 6422—
Product2-(4-Fluorobenzyl)-8-hydroxy-6-methyl-2,3,4,4a,5,6-hexahydro-2,6-naphthyridine-1,7-dione-5-carboxylic acidHCID 69069183—

Reaction Steps

A solution of 5-(tert-butyloxycarbonyl)-2-(4-fluorobenzyl)-8-hydroxy-6-methyl-2,3,4,4a,5,6-hexahydro-2,6-naphthyridine-1,7-dione, Diastereomer 1 from Example 4, (0.015 g, 0.037 mmol) in 50% TFA in CH2Cl2 (2.4 mL) was stirred at room temperature. After 1.3 hours, TFA acid (0.5 mL) was added to the reaction mixture. After 48 hours, the reaction mixture was concentrated under vacuum to give the title compound. ES MS M+1=349.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07619086B2
Source datasetuspto-grants-2009_11
ORD IDord-73bc0118e28749b19840ae591e7a6f0c
Source noteuspto-grants-2009_11