Diisopropylethylamine → HCID 57983510, compound

HRID 2078323Notes

Reaction equation

HRID 2078323 reaction equation
CCN(C(C)C)C(C)C.[OH:10][C:11]1[C:12]2[CH:13]=[CH:14][CH:15]=[N:16][C:17]=2[C:18]([CH3:28])([CH3:27])[C:19](=[O:26])[C:20]=1[C:21]([O:23]CC)=O.Cl.[C:30]([O:34][C:35](=[O:38])[CH2:36][NH2:37])([CH3:33])([CH3:32])[CH3:31]>O1CCOCC1>[OH:10][C:11]1[C:12]2[CH:13]=[CH:14][CH:15]=[N:16][C:17]=2[C:18]([CH3:27])([CH3:28])[C:19](=[O:26])[C:20]=1[C:21]([NH:37][CH2:36][C:35]([O:34][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:38])=[O:23]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 57983519HCID 57983519, compound

Product 1

HCID 57983510HCID 57983510, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

DIPEA (0.05 mL, 276 μmol) was added to a stirred mixture of ethyl 5-hydroxy-8,8-dimethyl-7-oxo-7,8-dihydroquinoline-6-carboxylate (24 mg, 92 μmol) and glycine tert-butyl ester hydrochloride (38 mg, 230 μmol) in 1,4-dioxane (3 mL). The reaction mixture was then stirred at 75° C. for 1.5 hours. The reaction mixture was concentrated, and the residue was purified by silica flash chromatography (0-75% EtOAc/hexane) to give the title compound as a crystalline white solid (15 mg, 47%). MS (m/z)=347 (M+H)+. Calculated for C18H22N2O5 346.4.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica flash chromatography (0-75% EtOAc/hexane)

Sources & evidence

ORD record
ord-a4845455745246789ea7283199843ce9
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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