Sodium Hydroxide → (R)-tert-butyl 2-(6-fluoro-3-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-3-methylbutanoate

HRID 1968259Notes

Reaction equation

HRID 1968259 reaction equation
[F:1][C:2]1[C:11]2[CH2:10][N:9]([C@H:12]([CH:20]([CH3:22])[CH3:21])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:8](=[O:23])[C:7]3=[CH:24][N:25](S(C4C=CC(C)=CC=4)(=O)=O)[C:5]([C:6]=23)=[N:4][CH:3]=1.[OH-].[Na+]>CO>[F:1][C:2]1[C:11]2[CH2:10][N:9]([C@H:12]([CH:20]([CH3:21])[CH3:22])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:8](=[O:23])[C:7]3=[CH:24][NH:25][C:5]([C:6]=23)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58293424(R)-tert-butyl 2-(6-fluoro-3-oxo-1-tosylpyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-3-methylbutanoate

Product 1

HCID 67224824(R)-tert-butyl 2-(6-fluoro-3-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-3-methylbutanoateYield 60.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of (R)-tert-butyl 2-(6-fluoro-3-oxo-1-tosylpyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-3-methylbutanoate (933 mg, 1.860 mmol) in MeOH (4 mL) was added aqueous NaOH (1N, 2 mL). The reaction mixture was stirred at 25° C. for 40 min. The reaction was partitioned between DCM and brine. The organics were dried over MgSO4 and concentrated. Purification by silica column chromatography (MeOH/DCM, 0-5%) afforded the title compound as a yellow oil (0.39 g, 60.4%). [M+H] calc'd for C18H22FN3O3, 348; found, 348.5.

Workup

  1. customThe reaction was partitioned between DCM and brine
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated
  4. customPurification by silica column chromatography (MeOH/DCM, 0-5%)

Sources & evidence

ORD record
ord-e95f8cf605364eefbbb804dba85634e8
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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