Diisopropylethylamine → HCID 67099725, compound

HRID 2078145Notes

Reaction equation

HRID 2078145 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]([F:35])([F:34])[C:12]1[CH:26]=[C:25]2[C:15]([C:16]([OH:33])=[C:17]([C:28](OCC)=[O:29])[C:18](=[O:27])[C:19]32[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:14][CH:13]=1.Cl.[C:37]([O:41][C:42](=[O:45])[CH2:43][NH2:44])([CH3:40])([CH3:39])[CH3:38]>O1CCOCC1.CCOCC>[F:10][C:11]([F:34])([F:35])[C:12]1[CH:26]=[C:25]2[C:15]([C:16]([OH:33])=[C:17]([C:28]([NH:44][CH2:43][C:42]([O:41][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:45])=[O:29])[C:18](=[O:27])[C:19]32[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099747HCID 67099747, compound

Product 1

HCID 67099725HCID 67099725, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

DIPEA (0.931 mL, 5.35 mmol) was added to a mixture of ethyl 7-trifluoromethyl-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-carboxylate (1.32 g, 3.56 mmol) and glycine tert-butyl ester hydrochloride (0.717 g, 4.28 mmol) in dioxane (30 mL). The reaction mixture was stirred at 75° C. for 17 hours. The reaction mixture was 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 desired compound as a light yellow solid (1.29 g). MS (m/e)=456.2 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-b6fefc9200c44c9e8d237de2c080c0e2
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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