1,4-Dioxane → 1,1-dimethylethyl N-((5-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

HRID 1868832Notes

Reaction equation

HRID 1868832 reaction equation
CCN([CH:7]([CH3:9])[CH3:8])C(C)C.Cl.[NH2:11][C@H:12]([C:17]([OH:19])=[O:18])C(C)(C)C.[F:20][C:21]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:22]=1[C:23]([OH:39])=[C:24]([C:34](OCC)=[O:35])[C:25](=[O:33])[C:26]2([CH3:32])[CH3:31].O1CCOC[CH2:41]1>>[F:20][C:21]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:22]=1[C:23]([OH:39])=[C:24]([C:34]([NH:11][CH2:12][C:17]([O:19][C:7]([CH3:8])([CH3:9])[CH3:41])=[O:18])=[O:35])[C:25](=[O:33])[C:26]2([CH3:32])[CH3:31]

Participants

5

Reactant 4

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 123146853-Methyl-L-valine hydrochlorideHCID 67099744Ethyl 5-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate

Product 1

HCID 670996891,1-dimethylethyl N-((5-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate

Procedure

DIPEA (0.14 mL, 809 mmol, tert-butylglycine hydrochloride (136 mg, 809 μmol), and ethyl 5-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (150 mg, 539 μmol) were heated to 75° C. in dioxane (4 mL) for 3 hours. The resulting mixture was cooled to room temperature and concentrated in vacuo. The residue was purified by flash chromatography to give 116 mg of 1,1-dimethylethyl N-((5-fluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate as a white solid. MS m/e=386 (M+Na)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b3f7439d012c490d8cef301b98334215
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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