Diisopropylethylamine → HCID 67099637, compound

HRID 2078141Notes

Reaction equation

HRID 2078141 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:25]=[C:24]2[C:14]([C:15]([OH:32])=[C:16]([C:27](OCC)=[O:28])[C:17](=[O:26])[C:18]32[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:13][CH:12]=1.Cl.[C:34]([O:38][C:39](=[O:42])[CH2:40][NH2:41])([CH3:37])([CH3:36])[CH3:35]>O1CCOCC1.CCOCC>[F:10][C:11]1[CH:25]=[C:24]2[C:14]([C:15]([OH:32])=[C:16]([C:27]([NH:41][CH2:40][C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:42])=[O:28])[C:17](=[O:26])[C:18]32[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099306HCID 67099306, compound

Product 1

HCID 67099637HCID 67099637, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

DIPEA (0.693 mL, 3.98 mmol, 1.5 eq) was added to a mixture of ethyl 7-fluoro-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-carboxylate (850 mg, 2.65 mmol, 1.0 eq) and glycine tert-butyl ester hydrochloride (0.534 g, 3.18 mmol, 1.2 eq) in dioxane (20 mL). The reaction mixture was stirred at 75° C. for 17 hours. The reaction mixture was then cooled to room temperature and concentrated in vacuo to give a yellow solid. The crude solid was suspended in ether and filtered to give the title compound as an off-white solid (703 mg). MS (m/e)=406.2 (M+H)+.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto give a yellow solid
  4. filtrationfiltered

Sources & evidence

ORD record
ord-5c876a0f6fef4a58b4128ed3602b64b1
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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