Diisopropylethylamine → HCID 67099911, compound

HRID 1868729Notes

Reaction equation

HRID 1868729 reaction equation
CCN(C(C)C)C(C)C.[Cl:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([OH:30])=[C:16]([C:25](OCC)=[O:26])[C:17](=[O:24])[C:18]2([CH2:22][CH3:23])[CH3:21])=[CH:13][CH:12]=1.Cl.[C:32]([O:36][C:37](=[O:40])[CH2:38][NH2:39])([CH3:35])([CH3:34])[CH3:33]>O1CCOCC1>[Cl:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([OH:30])=[C:16]([C:25]([NH:39][CH2:38][C:37]([O:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:40])=[O:26])[C:17](=[O:24])[C:18]2([CH2:22][CH3:23])[CH3:21])=[CH:13][CH:12]=1

Participants

5

Reactant 3

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

Product 1

HCID 67099911HCID 67099911, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

DIPEA (0.253 mL, 1.45 mmol, 1.2 eq) was added to a mixture of ethyl 7-chloro-1-ethyl-4-hydroxy-1-methyl-2-oxo-naphthalene-3-carboxylate (373 mg, 1.21 mmol) and glycine tert-butyl ester hydrochloride (0.243 g, 1.45 mmol) in dioxane (8 mL). The reaction mixture was stirred at 80° C. for 3.5 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo to give a yellow oil. The crude oil was purified by silica flash chromatography (0-75% DCM/hexane) to give the desired compound as a white solid (407 mg). MS (m/e)=338.1 (M+H-tBu)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto give a yellow oil
  4. customThe crude oil was purified by silica flash chromatography (0-75% DCM/hexane)

Sources & evidence

ORD record
ord-bdee3b8f0b144ca8bdea5ed80d878895
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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