Diisopropylethylamine → HCID 67099874, compound

HRID 1868659Notes

Reaction equation

HRID 1868659 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([OH:12])=[C:7]([C:13](OCC)=[O:14])[C:6](=[O:18])[C:5]2([CH2:20][CH3:21])[CH3:19].[ClH:22].[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>[Cl:22][C:11]1[CH:10]=[C:9]2[C:4](=[CH:3][CH:2]=1)[C:5]([CH2:20][CH3:21])([CH3:19])[C:6](=[O:18])[C:7]([C:13]([NH:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:14])=[C:8]2[OH:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099311HCID 67099311, compound

Product 1

HCID 67099874HCID 67099874, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of ethyl 6-chloro-4-ethyl-1-hydroxy-4-methyl-3-oxo-naphthalene-2-carboxylate (0.5 g, 2 mmol), and tert-butyl 2-aminoacetate hydrochloride (0.4 g, 2 mmol) in 5 mL dioxane, was treated with N-ethyl-N-isopropylpropan-2-amine (0.6 g, 5 mmol). The resulting mixture was warmed to 95° C. and stirred for 4 hours, M+Na=416, M−1=392. The mixture was then cooled to room temperature and concentrated in vacuo. The crude product was purified by column chromatography eluting with 10-20% EtOAc/hexane to give 0.44 g of the title compound as a white yellow solid. MS m/e=416 (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 10-20% EtOAc/hexane

Sources & evidence

ORD record
ord-5c4afcefe27648a5b9ad491594ccc6f2
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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