Diisopropylethylamine → HCID 67099585, compound

HRID 1868686Notes

Reaction equation

HRID 1868686 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([C:6]([OH:21])=[C:7]([C:16](OCC)=[O:17])[C:8](=[O:15])[C:9]2([CH3:14])[CH3:13])=[CH:4][CH:3]=1.Cl.[NH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].C(N(C(C)C)C(C)C)C>O1CCOCC1>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([C:6]([OH:21])=[C:7]([C:16]([NH:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:17])[C:8](=[O:15])[C:9]2([CH3:13])[CH3:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099634HCID 67099634, compound

Product 1

HCID 67099585HCID 67099585, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of ethyl 7,8-difluoro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (0.46 g, 1.6 mmol) and tert-butyl 2-aminoacetate hydrochloride (0.39 g, 2.3 mmol) in 2 mL dioxane was treated with N-ethyl-N-isopropylpropan-2-amine (0.60 g, 4.7 mmol). The mixture was warmed to 85° C. and stirred for 15 hours, M+Na=404, M−1=380. The mixture was then cooled to room temperature and concentrated in vacuo. The crude product was purified by column chromatography eluting with 10-30% EtOAc/hexane to give the title compound (0.53 g) as a pale yellow solid. MS (m/z)=404 (M+Na)+.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by column chromatography
  4. washeluting with 10-30% EtOAc/hexane

Sources & evidence

ORD record
ord-c91eb24a89ce428d9425845b83b33438
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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