Diisopropylethylamine → HCID 67099814, compound

HRID 1868716Notes

Reaction equation

HRID 1868716 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)([CH3:12])[C:7](=[O:20])[C:6]([C:21](OCC)=[O:22])=[C:5]2[OH:26].Cl.[C:28]([O:32][C:33](=[O:36])[CH2:34][NH2:35])([CH3:31])([CH3:30])[CH3:29].CCN(C(C)C)C(C)C>O1CCOCC1.O>[Cl:19][C:16]1[CH:15]=[C:14]2[C:13](=[CH:18][CH:17]=1)[C:8]([C:9]1[CH:10]=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=1)([CH3:12])[C:7](=[O:20])[C:6]([C:5]([NH:35][CH2:34][C:33]([O:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:36])=[O:26])=[C:21]2[OH:22]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099365HCID 67099365, compound

Product 1

HCID 67099814HCID 67099814, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of ethyl 6-chloro-1-(4-chlorophenyl)-4-hydroxy-1-methyl-2-oxo-naphthalene-3-carboxylate (0.998 g, 2.55 mmol), glycine tert-butyl ester hydrochloride (0.513 g, 3.06 mmol), and DIPEA (0.889 mL, 5.10 mmol) in 1,4-dioxane (15 mL) in a 75 mL sealed vessel was stirred at 120° C. for 3 hours. The solution was diluted with deionized water (75 mL) and extracted with DCM (2×50 mL). The combined organic layers were then washed with brine (50 mL), dried over MgSO4, and concentrated in vacuo to give 1.42 g crude product. The crude product was purified by flash column chromatography (silica, 0-25% DCM in hexane) to give the title compound (0.888 g). MS m/e=420 (M+H-tBu)+.

Workup

  1. extractionextracted with DCM (2×50 mL)
  2. washThe combined organic layers were then washed with brine (50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give 1.42 g crude product
  6. customThe crude product was purified by flash column chromatography (silica, 0-25% DCM in hexane)

Sources & evidence

ORD record
ord-010da88b4eb54c46906b0f9329b951f5
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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