Diisopropylethylamine → HCID 67100084, compound

HRID 1868752Notes

Reaction equation

HRID 1868752 reaction equation
CCN(C(C)C)C(C)C.[OH:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:18][CH:19]=2)[C:14]([CH3:26])([CH3:25])[C:13](=[O:27])[C:12]=1[C:28](OCC)=[O:29].Cl.[C:34]([O:38][C:39](=[O:42])[CH2:40][NH2:41])([CH3:37])([CH3:36])[CH3:35]>O1CCOCC1>[F:22][C:21]([F:24])([F:23])[C:17]1[CH:16]=[C:15]2[C:20]([C:11]([OH:10])=[C:12]([C:28]([NH:41][CH2:40][C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:42])=[O:29])[C:13](=[O:27])[C:14]2([CH3:26])[CH3:25])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099630HCID 67099630, compound

Product 1

HCID 67100084HCID 67100084, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

DIPEA (1870 μL, 10738 μmol, 2.5 eq) was added to a mixture of ethyl 4-hydroxy-1,1-dimethyl-2-oxo-7-(trifluoromethyl)-naphthalene-3-carboxylate (1.41 g, 4295 μmol) and glycine tert-butyl ester hydrochloride (864 mg, 5154 μmol) in dioxane (50 mL). The reaction mixture was stirred at 75° C. for 15 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo to give a yellow solid. The crude solid was purified by silica flash chromatography (0-40% DCM/hexane) to give the desired ester as a white solid (380 mg). MS (m/e)=358.1 (M+H-tBu)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto give a yellow solid
  4. customThe crude solid was purified by silica flash chromatography (0-40% DCM/hexane)

Sources & evidence

ORD record
ord-e4befc9f7ccf4e79a2162d7d779ac562
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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