Diisopropylethylamine → HCID 67099681, compound

HRID 1868682Notes

Reaction equation

HRID 1868682 reaction equation
[F:1][C:2]1[C:3]([OH:21])=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH3:13])([CH3:12])[C:9](=[O:14])[C:8]([C:15](OCC)=[O:16])=[C:7]2[OH:20].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:3]([OH:21])=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH3:13])([CH3:12])[C:9](=[O:14])[C:8]([C:15]([NH:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:16])=[C:7]2[OH:20]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099664HCID 67099664, compound

Product 1

HCID 67099681HCID 67099681, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of ethyl 8-fluoro-4,7-dihydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (0.4 g, 1 mmol) and tert-butyl 2-aminoacetate hydrochloride (0.3 g, 2 mmol) in 2 mL dioxane, was treated with N-ethyl-N-isopropylpropan-2-amine (0.5 g, 4 mmol). The resulting mixture was warmed to 85° C. and stirred for 4 hours, M+Na=402, 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 0.4 g of the title compound as a pale white solid. MS (m/z)=378 (M−1)−.

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-dbb3770a3be3494b90dea16a094e007f
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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