Diisopropylethylamine → HCID 67099939, compound

HRID 2078116Notes

Reaction equation

HRID 2078116 reaction equation
[Cl:1][C:2]1[C:11]([Cl:12])=[C:10]2[C:5]([C:6]([OH:21])=[C:7]([C:16](OCC)=[O:17])[C:8](=[O:15])[C:9]2([CH3:14])[CH3:13])=[CH:4][CH:3]=1.Cl.[C:23]([O:27][C:28](=[O:31])[CH2:29][NH2:30])([CH3:26])([CH3:25])[CH3:24].CCN(C(C)C)C(C)C>O1CCOCC1.O>[Cl:1][C:2]1[C:11]([Cl:12])=[C:10]2[C:5]([C:6]([OH:21])=[C:7]([C:16]([NH:30][CH2:29][C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:31])=[O:17])[C:8](=[O:15])[C:9]2([CH3:13])[CH3:14])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 67099792HCID 67099792, compound

Product 1

HCID 67099939HCID 67099939, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of ethyl 7,8-dichloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate (0.200 g, 0.456 mmol), glycine tert-butyl ester hydrochloride (0.0993 g, 0.592 mmol), and DIPEA (0.159 mL, 0.911 mmol) in 1,4-dioxane (5 mL) was heated to 120° C. in a 15 mL sealed vessel for 3 hours. The reaction was then diluted with deionized water (50 mL) and extracted with DCM (2×50 mL). The combined organic layers were washed with deionized water (50 mL) and then with brine (50 mL). The organic layer was then dried over MgSO4, concentrated, and dried in vacuo to give 0.338 g of the crude product. The crude product was purified by flash column chromatography (silica, 0-50% DCM in hexane) to give the title compound (0.185 g). MS m/e 412 (M−H)−.

Workup

  1. customsealed vessel for 3 hours
  2. extractionextracted with DCM (2×50 mL)
  3. washThe combined organic layers were washed with deionized water (50 mL)
  4. dry with materialThe organic layer was then dried over MgSO4
  5. concentrationconcentrated
  6. customdried in vacuo
  7. customto give 0.338 g of the crude product
  8. customThe crude product was purified by flash column chromatography (silica, 0-50% DCM in hexane)

Sources & evidence

ORD record
ord-93dcd5d15e7541f4b1409f9ca01273e8
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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