Diisopropylethylamine → HCID 67099829, compound

HRID 1868741Notes

Reaction equation

HRID 1868741 reaction equation
CCN(C(C)C)C(C)C.[Cl: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>[Cl: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 67100083HCID 67100083, compound

Product 1

HCID 67099829HCID 67099829, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

DIPEA (1.47 mL, 8.42 mmol, 1.5 eq) was added to a mixture of ethyl 7-chloro-4-hydroxy-2-oxo-2′,3′,5′,6′-tetrahydro-spiro[naphthalene-1,4′-pyran]-3-carboxylate (1.89 g, 5.61 mmol, 1.0 eq) and glycine tert-butyl ester hydrochloride (1.13 g, 6.73 mmol, 1.2 eq) in dioxane (50 mL). The reaction mixture was stirred at 80° C. for 3 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 ester as a white solid (2.23 g). MS (m/e)=422.2 (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-c8cdd2b62f234fc98d24348e2edb4c5a
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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