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

HRID 1436884Notes

Reaction equation

HRID 1436884 reaction equation
C([O:5][C:6]([CH:8]1[N:17]([CH3:18])[C:16](=[O:19])[C:15]([OH:20])=[C:14]2[CH:9]1[CH2:10][CH2:11][N:12]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[C:13]2=[O:21])=[O:7])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][N:12]2[CH2:11][CH2:10][CH:9]3[C:14](=[C:15]([OH:20])[C:16](=[O:19])[N:17]([CH3:18])[CH:8]3[C:6]([OH:7])=[O:5])[C:13]2=[O:21])=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 547137575-(Tert-butyloxycarbonyl)-2-(4-fluorobenzyl)-8-hydroxy-6-methyl-2,3,4,4a,5,6-hexahydro-2,6-naphthyridine-1,7-dione

Product 1

HCID 690691832-(4-Fluorobenzyl)-8-hydroxy-6-methyl-2,3,4,4a,5,6-hexahydro-2,6-naphthyridine-1,7-dione-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent2×

Procedure

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.

Workup

  1. waitAfter 48 hours
  2. concentrationthe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-73bc0118e28749b19840ae591e7a6f0c
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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